OPHTHALMIC LENS OR FLAT AND PYRAN COMPOUND

D sec

ritl

Patent the

Inve

tion of the glottis VMDK!

¿IOA

or PI and the

üCOIí9_OSTO

IR the " background P V-Y-NC past; the ES % the invention is disclosed-fo-o - r %

ivas

lenses and compounds f %

ocrômioom

•to arrangements for i % emblazon the legen % and

fo %o

it re8% ivas, D.

scrioã

. to the, T-front the

cniçs

!and % s

fo %o

L-

ea %iva

? 1 eCACC

'e

% commercial Kon Macintosh II TO is legen % e8

qae

darken in the sunlight and is left in the covalent

olareiam

'S interlinked from spec it

,oillz

and forming 1 - m to revise

sível

particle HE proves the

prtir

S %

halogens

of the sculptures bring the darkening of the n=% s. L..The plastic lens

apressn

%% the initialization the van - Gen. with respect to glass;

iorlnoi

between 8 0 more lead (

çar

%

icularmen

% and in the case of lenses Separation %

ílmicas

having a degree strong) 8% less

snsoepívels

the broke "because the action above

dsscri

% the salts sculptures dispersed alkali the

ooorre

arrays and L Monday the co•° bend is

fe.i

% sec attempts to % IV and to develop compound

fotoor

ECO Q-

proaU

could go m" the the effect in m " Kent

i.s

the ballistic

ecmpostoiò

L. w E EST mapping RFF should have, when absorbed TOs coated covers a plastic lens

oonvenclonal

, the following

propríeaades

, i.e.:the

rendim

(a) one al % of n % the quantum to color near ultraviolet, " (a b) a low

rendlmen

% the quantum of whitening with visible light, (L) a

rãpiŒoaesaparecimentoermmco

% at ambient temperatures..Unfortunately, these properties are generally U-claims superior

assooladae

w % thermal or photochemical

abilidaãe

plugins, the blank which V saturation "" streamline % yl of spectacles incorporating these ultraviolet absorbing compound is very short pr

apliaç

the trade.US alkali 3,567,605 (Becker's) describes

sérd.e

TMA-pyran derivatives " including the benzofused each!the SLS

olranos

and %!

oirauos

but the spiro-

eompo

multicasts, demonstrated that 9

príedadesfotooremlcas

. These may be considered the composed %. as

asrivadosoromeno

of 6 typically, o3 compounds safe a change from colorless to yellow-orange upon light irradiation D.V.. However, observing this

compoT

% adhere by Becker's was limited at temperatures below about - de - 40° from 0'S

reglstrou

Becker in that the color change was reversed when the temperature was

elsvaãa

at the 37oC °u e - 10.PadaWan et al reports, in OJ RO Cho-, volume. 40, the N-O 8, 1975, pp. 14 2, we examine the kibbles compounding photochemical multicasts the type described RO Becker's, identifies products•amu

eriu

- age of the air for N

ermedcoloriãom

abortions ring ethers

fenólicoe

not

coloridoefluais

. The colored forms were examined by

adwaInstavels

at room temperature, and this temperature it suggested that the colored regions of the subdirectories

intermediãri

-

lídi

the

ooloridoõu

CIP term

oamente

for raw materials or forested addition 1.4 solvent to form the corresponding product

metauol

phenolic ether, or a displacement I, 5-hydrogen in acetone to form the phenol

oorreeponden

E but ium, idler routes in neither suggests that the stability of

eompostos

it we could be improved nor any modification that could be done in the stature of known

oompoetos

of tyrant to the Indian

ziroomportamen

% the photo-

rea %ivo

in a plastic lens.Properties required of a

oompos

% for application in the eght

erômicoóculõs

absorbing are

descri

% the SRAs MA and the compound that properties were posted

eataeden_o

kingdoms compounds,,

heliocrômicos

,, in GB o2146327 alkali.Thus, the term "

helloorômleo

" used in this

eCmpostorelató

- a rare river

eignifiearoomDosto

that powders of Ti the following

propriededee

or if the (a) a

élevadaefioiênoiaquântioa

to color near the ultrasonic

vloleta

, (a b) a low quantum yield pair whiten with white visible and to ITL (o) R Fast

termião

disappearance in room temperature, mAmp not so lukewarm so that whitening in white light and heating

térmioo

prevent

ooloraçãooomponente

UV at, sunlight pulls. arrows

propriedmdes

make eminently

alOropriado

compound for use in slow picture of-reactive.patent application no. 8611837 @ b of the applicant, or U.S. brr PP 87,025 11,

descrove

it XO a

sorze

••of

eopiro

go to m nodes that 2 year

fotooroossBuem

properties L. 1 00 tlaughed servers have no AB 0

deeeõáveia

, described above, in

eonuuto

with good thermal stability and the

oquímios

%. These

espiropiranos

of

adamautauopoàom

also be

ínoorporados

slow plastic materials in patterns, as

GR59

, padding the elements have been found to be this

s6ríe

oThe

azes

of undergoing - - - numeric Range number of cycles without degradation

signifloante

.Teaches that the reason the

eompostos

in above the applicant demonstrate these enhanced properties is "Q is, to the rule of the

Bredt

, the spiro - - carbon cannot become doubly bonded and" thereby

colorlaa

ring abortion is resistant degradations associated with

ãeslooamento

of 1.5-hydrogen.but the, limiting donate contest

Œes

% the series is that the contest demonstrating improved resistance to degradation in demonstrate a color change UV exposure (or sunlight) the

inool

R for yellow-orange. The dema1 wool market, in ' but, 6 much larger pair

lenteo

that

esoureoem

for

marrem

or gray=despite, as indicated "in coassigned

Rondente

Applicant's Psalm" a lens photo-festive refastenably produced by incorporation of n lens from a ReportingJBoss % Phew a om - the f % yellow and a blue

oerômieo

., in effect the EER % COL 6emon

troueilíail

prepare photochromic compounds and purple/blue colored, whose

reslstênola

degradation hi fatigue was equivalent of'S improves. among the s

iropi

: a1 the

cõlo

going yellow.the AA summary L.

venoEo

of

e.cordo

with one aspect of the present invention, it is a press

len %e

or lens Separation %

álmicaescureee

that in sunlight and reverses pair 1 mA clear condition. in white or colorless light volts in %%

smpera

amu frogs

normsis

environments, in Q and the lens in the RO

iucor

% therein, or having % gone thereon, at least oompo9% hurts the

helioorômioos

, amu " R %

ferldos

comprising composite

esDirobenzoprano

of me

adsmantano

or

espS.ro

it

naftopirano

in a group the initialization it

_n %ano

and's "

resen

% and position 2 spiro ring

benzopiropirano

% SLS in or" and m 8e oThe 280a so the % comprising the

benzoounaftopirano

me having a replacement -%

uintenitrogenxo

containing at position 2 ring compounds and the tyrant tyrant by staining of D invention are based s at Me and UK % RH s stumble Bs 8icas " as the spiro tyrant of

adaman

%% in the ylidene

descri

the EO-pending above the

requeren

% e°?eRA

faeilidsJ

of of the

debcriç

, the same

Oóe

"

LgO

be aggregate as in copending application

requerent_

pr designate

estrumara

sec toluene basic and the Axis alkali arrow U of the to discern the h. post % XO tacky colored"

zul

% en8o a inc. -%%% I to

uin

and

oon

the endo % nitrogen, the % s:The h07

HgSN

X-R 1 above formulas'S r 1 al reports the GI

uila

glycolate X-X represents a group having a glycolate from UBS -%%% I to

uin

and contain hydrogen. 0% lay

represen

group for R % be foreshadowing

smbém

a

grUl

:, the curry

suhs

having a % I to %

uin

and

oonl

;

ezzd.onitx

it - -

êlXi

the,, R is and lower

alç81ila

reference, I to RO example catch % yl,, % and yl, phenyl and X is 0%% poppy, of

preferênoia

, a phenyl group having a substituent containing

mi_trogênio

at position the food or for, example a group RO

atai_

. in,

mcrfolino

,

piperidino

, II.

irldino

, RT

irazolinoirrol±

Iunatics primary, secondary %

eroi

river. however, the R-L

esen %arpoãe

SR still a phenyl group having a

sabstitdinte

containing

rogênio

% similar in position RO

oou

% to -.In the case where the group EU glycolate

reRresen

lay by the separating " II x has a s1

ints

of 1% SB highlighters

itrcgênioheterooíolioo

ring in the R 0 1

Csi9ãocri

!- expensive, the

bsti

%

uinte

heteroalkane - cyclic group is

ligsdo

at

asila

through the atom -

mitrogênio

ring. The Serres•. 1|

piranosheliocrêmioos

that are currently of the imparted are the Serres•

hõ7n

° from of the compounds.A wide variety of % s is possible

snbstituin

benzopyran in rings and

naftopirano

of these compounds. rO example, if

eonslderar

the

oompos

% the

HOTN

series,

tendõ

the following immature O "

aala

general:The R 5 R-R-R 4 6 9 positions represented by and s 1 and the

lOOdem

be

seleoionadas

from hydrogen, alkyl, (.

preferivelmen

% and lower alkyl, this' is, I to 5 carbon atoms), aralkyl, glycolate (including substituted phenyl), alkoxy, hydroxy, alkyl or d/

alquilem

!in, W

uilsminofenila

, halogen or groups hrs %

erocíclicos

, with the R-U-

eundição

@ 3 can have the R 4 is not

alcoxl

,

hldroxi

or

alquilouõlalqullamino

. examples of G

upos

heterocyclics are furyl or thienyl groups, preferably, the R i1 3 e 4 are both

hldrogênio

L.

orqus

the inc.% I to %

uintes

at these positions may provoke yn % and feeds sternum-o

tímicas

undesirable colored form produced in ring opening of the

piranoosubs %

-I last

atiçooiDosições

in other than the R position 6 has influence on the behavior saves fo-h.

mioo

of the compounds. but, the 8ubs % I to 6% in the R position

ulção

has an influence on the behavioral compounds IVa

slgnifica

% f %

oer¢

I to those with 1% of the

os.exem

- by " cutting, introducing a group release Tysons % theft is his, as U-

ulntemlbsti

% r6 I to produce a position deviation in

batoorômiooespeetro

of

absorção.da

form

oolox

' forward. Examples DSS-' those guys

uJ.ntes

% replacement are

alquàlamino

,

dialmlil

me - in 8m

nofenila

,

slooxislooxlfemila

or al %

tiloudialqu_i

II

nofenila

initialization, the series of compounds demonstrates a hr urg

res9o_s

RT

heliocrômina

from colorless to blue or blue in the light/

írpura

'S

olsm

, dependent on solvent % die PL

s %

it ECO in q1 and

oomposto

is held. Properties

esmaeclmento

. the compounds of the

téraiso

h071'S

a9ropriadas

generally for use in LT 0 01 O'S 9ara sol and the

eflcaclas

of a Bran -

queamento

in daylight

d.lfusa

at ambient temperatures " appear to be higher than the corresponding compounds of the EU hc7. In addition the

resls

%

enela

fatigue is good and the

eompo_s

mappings can be incorporated but plastic lens by

técni

oThe'S IM?sR

mçãodesczüta

in co-pending above the applicant. the n PP " inc1 it, every material•8•

lastlco

•.having desired properties O %

icas

L.

ocle

be used to the array lenses according to this invention. examples I include lenses bicarbonate and methacryl % O and % the acci yl methyl 0% material more

oomumen

is used pair lens 1%

lásicas

(allyl carbonate) is His

d_ie

ylene glycol

almente

'S of known leveraged 0r it 39 (air-j9 is a mark of the SR Strad stolen

P.G

.7.1 d). Processes the lenses and

fabzloaçfabrioag

are e.g. the

descri

%=L the ene %% s U.S. 3,944.637, 2,542,386 and 3,404. 861, incorporated herein are soiled

desozüção

R-shotgun AB

rêncl

at many of the compounds containing the

plz¿

% NL border

rogî

- EU are the

descri

%%

exmos

into large series

HülN

, et cetera, are novel sompo8tos

qo

mls. Sew in accordance with another aspect of the invention, thus, 1

OrOVê

a RIP

Lnohelioorômloo

%

sndo

the O 1 general no (L separatory.&) (

ZZA

) I to 9% the R the R "wherein R 3 river have the FGI the Li hoist] the indicated above, R is alky wool, R." represents one or more

oubs %

it

i %uln

+. s

independen

%

emen

-% and selected from hydrogen, 8lq yl, halogen, wards XL at,, clay or a flu product

heteroclclioo

, w•and each Y represents.de l'

ndeendentementehidrogênlo

, amino or alkyl, or flu product or a

dlalqUil

Miño

heterocíelicooontenclo

Ni-

rogêmio

%, with the proviso that, at least, one of Y is a group.sampling, and in-that the ring containing the inc.% R-

ituinte

'

oàe

be

benzauele

and LOI Ill w 10 heterocyclics are spear

femila

, thienyl and

plrrila

.. The invention

sambeminelulpirauoehellocrômlcos

I wasn f

oraulageTg

. iI:(Zα) Y R-EU, R. "and Y have the same

eignifieado

11e above in

fórmllla

(AIF) and R ' and R" represent one or more replacement

uintes

independently

seleoionados

%% of complexes, alkyl,

halogênío

,

aleoxl

,

arlla

MW ou warm or substitute or a group

heteroeíolico

(% 83. as furyl or

ienila

%).it is also possible to prepare a

serre.e

•multicasts

debie

-benzopyran times that are also offset blue. These multicasts the

eom

demonstrate a promising behavior of the RESIST

melh_o

insist in fairy Nolo of Fo

odegradaç

the %. This rotate

mtrgir

abrasiveness EE

±

Z-bermo2irano

itura

of surviving to cont-I last

nuar

to function after the first has been

degredadoeael

.iI must however, as spectrum will demonstrate bonded, the pepper

bisbenzo_niranosremoem

offering another Van de % act in Ue the was it but

inoolores

absorbs more strongly to

róximoul$ra

-violet than the colored forms,

assim_aume_n

sucker the conversion ARA form

oolorida

and drafting the effect

àe

inner filter.The naphtho-neck

piranos

are also new

compost¿

s and may be

representadõsseguine

by general formula (I-II) - wherein R is AL a

uila

or underarm and Z is hydrogen, alkyl or glycolate,

raTerivelmen

% and L deactivated least one of R and Z an f 111 1% phenyl St.

bsti

amu D. 0 group

EmLinorlm

- river, secondary or territory or a group

heterooíclloooon

%% 81% endohydrolysis IM

rogênio

as one of the grateful

heteroololieos

J.

meneionaaos

above. The naphthalene ring may contain

substituin

s % s as the disclosed by R ' in formula (IA cations).Serial

ntese

'S hc7n of compounds s % s om the % the can be prepared by a portion can have it array

OlaisenmodifioaŒa

, shotgun

clesori

% knot

pedião

copending above the applicant for the appropriate phenol

rea9ão

an alcohol derivative RP 0 "1"

rgll

EO and.eTS repressurized Domo NA and the Rearrangement modify provides a Z EC EMI general GE for the preparation HE. the

oompos

-% of tyrant, comprising heating a phenol derivative common

propar

ofan appropriate in one-to-

olvente

oThe % in the presence of an appropriate reaction conditions

slisador

gentle.In contrast to the conditions in the reaction normally lend portion can have it arrangements

laisen

0, the process is performed in relatively low

temporalizas

, xylene or toluene in RO example boiling and in the presence of m U % 8iisadora9rogria O general AC, the temperature and relative should not exceed about lso by 0. e is not greater than the NCI -

prefe

160e0 or less is - "

tramenor

hardening.The relationship

pode.ser

expressed in % as to general wilderness - go II +

H0_

oThe > multimedia. (A) Hx samples " in EU (a) may be quality zeal and () or an alcohol

pmopar

ofan. a derivative such as

looolproparliooproparllco

#. The relationship and•catalyzed alumina and proceeds in the R %%%%% Element

empere

'S

ivemente

low a marked absence million and

lacerais

kibbles. In see acetate, and possible to use

quslç

tumors carboxylate

alif

%

ioo

or

aromtlco

, pr example propionate or benzoate.Partner'S

aumen

% yields the OB % ides using acetate

propargllico

and heating it with a phenol solvent such as xylene=min 11m

Ereeença

al1 acidic alkali of the n as " catalyst, sec

rgreendentemente

, s % the

eond_ições

917; cause a mild count can have it array

Olaisen

, while traditional&conditions and relative, e.g.

aquecenào

amu to about 2 in strongly acidic or basic conditions cause thermal

decompoaições

of the reactants and/or product

desejaào

.This process envisions 1, mA synthesis in a convenient

etapebenzoenaZto9iranosalquer

wide use it and the alcohol or acetate ofan pro-T-appropriate OTLs

citroàe

alcohol derivative 9 the Ro!rAG ofan.The acetates turvy

llleo

$

oclem

be pre - the.networks for relative one ketone appropriate calcium lily. A complex lithium and acetylene /% ylene

dlamina

and p

adioiona

&with stirring at the % cells anywhere

solngãoàa

ketone in an appropriate solvent, such as the or of

tetraldrofurasulfóxiàoimetila

. 0 product is the corresponding alcohol R-RP 09

llto

and the alcohol is conveniently

oonvBrtião

in acetate RO relationships with EtAc

±

wool chloride in an appropriate solvent.However they!the difficulty if f.%

uar

an efficient conversion of the {10

Iooolargílico

in acetate and subsequent separation the last, "and" desirable•'" utilize the

álcdol

1 ir liç 0 P/tool as a majority of I)

riæa

.

llooapropar

alcohols can be obtained by treatment of a ketone (folded and is substituted with a group containing nitrogen in the position or the RO of AZ) om a

oomlolexoaoe %

it

ileto

L of i-ium/

e %

it ylene diamine in an appropriate solvent.

Veriioou

to

rendlmen

% the

maroadnente

are improved if a dime sulfoxide yl is %% dry

isado

as solvent.Preparing the R series of 71 with

ostoszoações

is illustrated by reaction scheme shown in scheme 1 shows the I. the

reaçõe8

resulting in the formation derivative 2 it itl!0

eridinofenila

of

H07

, (the ' if m/go reference laughed h071 - 01).Referring to Scheme, i - l - (II)

i10eridinoacetofenona

is %

ratsdo

complex

ace %

it

ileto

lithium/

e %

it ylene

diamineo

to give the alcohol! 0 0 1 the Li

parg

the R " independently (2), the knot may be converted

ãlcool

Bandage % % (3) to the 0 II.reacted

diretamen

% and more with L-n8ftol (4) in the presence of acidic

alumin

. 0 initial product is

rovavelmente

ether property "" (FXO) suffering spontan %

aneamente

the

tedisposição

to form (6) hot ki.of L-naphthol (4b) (i0 gm) and a mixture 45:55

propmrgíllco

alcohol (folded) and - (II)

iolperlãinoacetofenoma

unreacted (20 gm) were dissolved in toluene (75 em3) nearly and the solution was adsorbed for

allm±

in activates the acidic (200 gm)

eemga.e

% DAA in a chromatographic column.these conditions

suves

tampon, the alcohol!0

roparglieo

•" (2) was reacted with L-naphthol (4b) for the

provavelmau

% and, O is % ofan

roparg

tumors (FXO) who has experienced spontaneously re-array

Clalsau

for hot ki (6b) the

proau

% was eluted from the column with the AA the cold toluene. The

fragõesfotoorômicasoomblnadas

were, of the R 1

coloridaBebuligão

with Smudge refreshed II? (4 gm) .and evaporated. 0

reszdao

F was

purifleado

for er - the %

ogz

'wool on alumina using a mix 1 -' 9 of

dlolorome

% year and hexane shotgun eluens % EO-hr 7 it ki (6b) was tampon % gone as an oil that defendant be nearly pure footprint % per-

espee %ros

- copy and repurpose "

m,

it

'z

° to impurity was a' the small amount of the unreacted starting ketone (II).•

rooedimen

% the like may be employed to make other more

oompos

% the in this series, the following examples to illustrate the data

a8ieionais

'S the preparation of the 10%% ro8 composed the s and 0

ífi

00 S of series

HC7N

, % EE and required in:

emplos

"the s % UK % ur8% of the SLS

opir

" and AE

equaçoes

of

reaçao

are

apz

"

eeèn

Partner

eegu

in %=

ín

'S

deeenhos

sheets.ReadyOww

aão

raw flexibly in the naphthol sec wa % highlighters gone right back to OH Me and 0h is

ilacKooxieloreto

phosphorus (319 gm, 1.6 mole) was

aclfoionaclo

in&pathways for 4 hr to a solution of Z

uetoxinaftalenoagtada

(250 gm) (2) dlmet13foz

amlda

(150 gm) dry MlS % IVR

reabro

gall

aqueoida

was a bath at speeds AU 9or heavier 4. hr,

resfrlsda

, and poured into ice (K-II) aqueous sodium acetate 2 min (1.5 II). The journalist ACS gall wandering with

dleloretauo

(I 1) and acid washed

eloràrloo

followed by the

lluágu.s

" The layer was extracted

orgêmleadiclorcmetauo

MT (I to II) with dilute acid

uvaça

and followed - AU, the organic layer (II s0 4)" filtered and the solvent removed.4 it

me %oxi

L-NSF Standard (3) of the outstretched DC was obtained a yellow oil the 4e % 0 XIa l1 AF lens (3) was 0

Ideíddlssolvldo

glycol (I to II) and hydrate (125 gm) was epaulet

ILidró

,, - - of the potassium (125 gm) was the

dloRonado

that was

aqueoida

to 200 - °0 for 5 hour, R. ReportingJBoss % Phew gall yo " of the cool, poured Serres

Eelo

(K-II)% with tumors. A single yellow - O that was separated as the

hldrazida

of 4 it

me %oxz

L-SLS % (8) Z-L-o°•separate the filtrate was filtered, the gall diddily (s0 4), IDF % s to 0 and the solvent residual

õleo

4 it

me %il

L-me %oxlnaf %ah0ah ° 2 c ± o Zao has Q-Z-CH3 of NME India it

e %ildifenilmetiŒenosucoínioo

% are tumors. (6) (i00 gm) was

àiesolvldo

in

ioo

%

acé

anhydride (250

cJu

3) and anhydrous sodium acetate (i00 gm) was

adlelonado

. The mixture was

aqueoida

was a water bath immature RO 6 hours and poured onto ice

resflrada

%% LR

uraQo

(K-II). The mixture was and optimize -%

raída

with

dioloro

% year (300 m3) and dried. (' gs0 4), filtered and the solvent removed.(7) the residual ether was

hidrolleadoebuligãosolugão

om in the hydroxide

ssloetanõlleo

the 104% (600 3) for 2 embroider, the majority of ethanol

fõiTemovIŒa

and the residue

aoidulado

om 5h

olorídrioo

acid. The oily acid (8) released was extracted into the Ro 0 -

fórmlo

(250 m3), dried (R. s0 4)" immature

±itrado

and solvent removed. 0% residue was crystallizing the pair go acetone giving

áoddo

4 it ham L-

hldroxi

it 3 it

naf$ólco

(8)

oomoum

pale yellow solid.Of the

soarboxllaç

0 1 0

kftóic

acid (8) (20 gm) was

dissolvide

in

quinollna

(150 em3) copper and bronze (20 gm) he stirs

adioionado

. The ReportingJBoss % Phew fu " boiled for 4 H and allowed to cool. " The mixture was filtered and the filtrate treated with acid optimize

aloríàrieo

51 and extracted with chloroform. The

trabslho

gave an oil (7 gm)

marremesouro

which contained 2% less than $- phenyl-l-naphthol (9). Failure

descarboxileção

stage is attributed to the quality of the phosphor bronze copper was used. sufficient product was obtained pair make 5 it

fenilbenzooromeno

(4d! PH of the R=) (see formula below).The Derives.

acutila

of "

lolldina

bromine (5 gm, soft 0,032) was dropwise with stirring at enthusiast a solution of julolidine (i0) (5 gm, 0.03 improperly)

èmelorcdormlo

. The addition was complete - botch, the mixture was stirred for 10 minutes.The orange color of the solution was discharged and a

sõlido

colorless if aro11. Other Shorten L-sodium bicarbonate solution (50 c 3 min) was added and the chloroform layer was separated, dried (II gs0 4), filtered and the solvent

removide

. The bromine-

julolldina

(L separatory) was obtained as a yellow oil

Relido

.(III) bromine-

julolidlna

(7.8 gm) was IDS -

solvida

in dry tetrahydrofuran (100 crude 3) is cooled °0 - a - 78. Under

nitrogêmio

, a solution of n-diethyl but!l. lithium ((20 in 3) U the solution 1.6 " in hexane) was

adioionada

, allowed for 1 hour nanodispersion % air, and then n, alkali

dlmeilacetamlda

(3.5 gm) was added dropwise. The mixture was husband a - 78 C.; 10 minutes RO is allowed to warm

empera

%%% and ARU

smbien

. The ReportingJBoss % Phew pool poured onto

Eelo

it it

%ri %urado

"F1 or" CA man % and

aeidulada

broth with fragrance D. ECO 2 and expired in tumors (2 x 100 cm3) is % 0%% Ill the WR is the % Er had dried (80 4), immature L.% and the solvent removed from shallow, leaving an ARU % sometimes referred 2:3 and

aoe

(12) yl-

julolldina

and bromine-

julolld

in unreacted (III) shotgun 4MU

srarelopálído

oil.The preparation complied alcohols

¿Œnofeilce

-% I to managing information on IBM ' mM KI U of the OH groups.I and it

C.O

to OH=0=0 hr > " ., - - - c5>IA cations CI - _ - _.The ID>© ME the O-H c=0. W=CH3 H and %% ET and eth 4 4b

¿

R is % 4d 3 - general procedure II the

aminofenilce

%% 1 MOA•

Nubs

- one part I) was dissolved min sulfoxide and yl

dlme

% if the E 2? the solution heated to 60 C

aeetile

complex % the lily /" and

ilez

%!the

dlsmlna

(part I) was

adicloŒado

in - L "

çoee

will agitate the solution in % T-al reports that the formula Xa % in!the n the

oeratva

rises above 75 - °0 nor dropped below 60 it 37oC. When addition was complete, the mixture was the datum highlighters - 60 - °0 for 3 H and then poured onto ice % I to %

urado

(6 - 8% s pair). The ReportingJBoss % Phew datum was Ill %

raŒda

with

dloloreme

in, the layer

organzoa

if!

oarad

dried over anhydrous

magnetizo

sulfate, and filtered, and the solvent provided

do.fil

% erate, The residue is alcohol

cetilênioo

usually with purity 90 1, based on the analysis of R % RO

espeeroscopia

, me, alkali. In the following

exemplòs

, Z's:

íduo

, after " solvent removal was %%% IR

uraão

PE

róleo

(P.E. Ugh. 60 - 80 - °0) 9m some cases " alcohol % ESA

ilênieosolidlflcou

waste and was.

filtz

' lay and washed one hundred petroleum cold {E 60 - 80 - o0) the his alcohol

acetilênleo

lay of crystallizing T-petroleum was removed and the oil

reeidual

used

dlresmen

%% EO-3.1. i - 2-O morpho!

inofeni

!

bu %.

it

_3_

it relative LU it 2 ol (3 0) (see above) (3b)

pTorfolinoacetofenona

(30 gm) was dissolve in

Bulfóxldo

of

dlme

%

±

wool (i00 in 3) and

comlol

exo isomers. :of the

aoetile

% L % and % ylene diamine/ium (30 gm) was added in portions to the solution 60 0p outpostand so that the temperature does not elevate above 75 - wa °0. As

Traba

-

Irando

deser1%%

proeedimen

knot the general described above ":(30) gave the alcohol as a yellow solid (25 gm, 80% w

rendim

the).3.1 ° 2.2 --p-

die %ileminofeuilbut

it 3 it the in-2 ol (40) (see above) complex of Ace %%% island but the L/ium and % ylene&razor (i00 gm) was added in small!to a stirred solution from GE

0orções

10 it

dle %ilvminoace %ofenona

(4b) (ii0 gm) south of P O gone

d.imeti

(300 in 3} the 60 -0 " a % in that the temperature does not hamper rises above 75 - °0. Working as

deecri

knot

procedlmen

%% the above general, gave the alcohol (4c) as

plaoassmarelas

w

lidae

(the pair % IR of petroleum, E 6 it 8 "the) (:) .25", 8 5 0

Gaiaena

).The \ O-H I to catch the n hr>beinghis?->and e is 55b ".3.1.3

Iãe

R. - - -

N.metilçiperazinofenilbut_

it 3 it the in-.2 it

çl

(5c). (see

aelma

) acetylene complex lithium/ethylene diamine (25 and) was

aŒielonaŒo

in small portions to a stirred 5 lution P n-

metilpirperazineacetefenona

(FXO). (25 gm) in

sulfóxide

of

dimeti

!the (250 in 3) 60 0 in such a rate that the annealing % Phew endpoint not brought above 75 @ - from.work as a knot

proceãimenŒescri

%% the overall pamper, gave the alcohol (50) with an I 0 O colorless (18. gm, 6" /% yield (purity of 9% +)..3•

¿

I - 2-n-

fenilpiperazinofenilbut

- - the in-2 ol (60) (see CA the) complex and calcium and lithium /% ylene

dlamlna

(38 gm) was

adleionado

in small

orçôesegl

% to a solution of the P-n-fide

ilpierazinoaee

%

ofenona

(6b) (38 gm) in

sulfóxiao

of

dlme

% L to (380 3 min) in the 60 0%%%

ãxa

al reports that the ARU rises not

empera

% choline j of 75 c° working as

aesori

knot

prooeaimen

%% the above general, 8eu (60) the alcohol as a yellow powder (27 and, surrendered - 68% (90% + purity) assembly.3 1.5 - 2-to - (l. 2.3o4 it

te %r

,

aidro

it 2yisoq

tinolinof

. enyl) - -

buç

- :. - .3: - 2 it describes (maw) (see above) complex of miney

iletoaoe

%% ethylene/ium

efemina

(26 gm).

adlc

was

±

love with in small portions' to a

eolu9ão

stirred p-2.2 3.4 it

tetraidroleoquinouoacetofenona

(TB engaging) (25 gm) in a dime of

eulfórixo

% yl (250 in 3) c in formula Xa % T-al reports that the temperature does not rises above 75 it a0. Working w ou described in the above general procedure, SAD (70) in the alcohol yield nearly who do BOI % labeling as a gum (22 gm) (90% + clarity) 3 . 1.6 - --p-

morfolinofenilloent

L-yn - - ol hydrochloride (80) (see above) complex of Ace %% the island but lithium and /% ylene diamine (20) was added m small!to a stirred solution of

oorções

>

morfolinopropiofenona

. (Sb) (20 gm) in dimethylsulfoxide (100 em3) yl % tell me the 60 -0 hamper such in - J...that the temperature does not rises above 75 - °0. Working as

desori

% in the general procedure above the " the D

áloooi

(8c) as an oil (21 gm, 92 1% the

dimen

) 95% purity +.3. I - 7 -

Imetileminofenil

the Ro,

pinol

(13.) (see above)•

amplexo

ACE %% of the island but miney ium and /% (20 gm) ylene

diamlna

was added in portions to a stirred solution of 8 min.% yl a dime

benzalde

D. 0 0 (20 gm) instructed 01 spec indeuterated 0% of a dime yl (80 min 3 3). When the distinction was

oomple

% T % Phew ReportingJBoss was 30 minutes 1 shakes the R•

aqueclda

then in a bath of water content by 15%

minu

PSO is cooled.Working C

deseri

knot

prooedlmen

%% the above general, gave the

ãloool

as yellow oil (13)

elido

(17 gm, 71% rend2men % the).The•repair D., and naphth 010 RL

ü

0 S of series hot-a-n ' (see formulae IMA) example 2, 6 it cl°r° it 2 it

me %il

it 2"..... , . -

morfolinofen

'

ilvenzocromeno

(3 ;-consumer the,) (see above) 0 a

olu

9 will of hot. alcohol 2 p-

morfolinofenilpr

09 0 (30) pyrrolidin liç (3 gm) and 4-chloro L-naphthol (3 gm) in toluene (75 crude 3) was plunged in a acidic alumina column (100 gm). The column was extracted using chloroform and the chloroform solution was! blushing. The residual oil was

lgurdflcado

by column chromatography over al m in, using

dlclorometano

and petroleum, E - 6080 °0 (1:20) as eluens % and, %. he3_iocrômica fraction was separated and the solvent removed. The

recrisalização

% of the residue from petroleum gave the

oror

.. (3d, r=01) Leh as a nearly colorless powder.2 6-dimethyl-2 it

morfolincfenilbenzocromeno

(3d|'r=e) (see above)•

icool

2-O

morfolinofenilproargíli

EO and (to) (8 gm) and 4 it

me'til

L-naphthol (5 gm) were dissolved in hot toluene (300 em3) and the solution added.. the

al1

m4ua dry acid (200 gm) in a flask equipped with condenser of n 1. The

mlst

will '

fci

(20 min.) in

aqueoida

% of a tack. to the AU, cooled and the IDF % rada° al1 m4ua

reaidual

was extracted with chloroform (3 x 100 oro3). The combined extracts were filtered

orgaracos

and an EVA!oThe Partner and the residual oil was by chromatography on alumina

impurificado¿

[(100 gm) U.S. cide

nãù

a mixture of 1:20

diclorome

% year E oil as eluent,

heliocrômica

fraction was separated and the solvent removed, leaving a brown oil I work.short chromatographic separations

uas

failed improving the quality of the

benzocromeno

(3d; " r=e).3b 0 oil

marremescureeeu

in air but if

espeo

% r6 NMR:

indleou

Bros of 5 of impurities.it

xem

4 2r6-dimethyl-2 p-

ale %alminqfenilbenzoerome

=R-Q water 4] from GE) (see above) U to hot solution of alcohol 2aie % I to 1 (40)

minofenilproparglioo

(15 gm) and 4 it

me %il

L-

naf %ol

(i0 gm) in toluene (200 were) was passed into a column (300) acidic

alumia

dry. The fraction was

heliocrmieaaluída

with

dlolorometano

and the solvent fight back. 0 residual oil was

±Purifoado

by

cldo

on alumina (300 gm) using a

Bolüção

chloroform (1:20) and petroleum shotgun " eluent. The fraction

helioerômioa

was evaporated and the residual colorless oil %

±

RO'S

alIza

the from PE %

róleo

giving, the chromen, (4d; the R=] the R from GE i=h) as nearly colorless

crlstsls

. 0% spectrum

qualita

BOI rim chloroform before and after exposure to a light and forming Gas flow network in Figure 7 we %.mPE, !the 6 F-enyl-L 2 it

me %i

L 2 - - dL and 1i L.|yne immature enyl BI

snz

the ol hydrochloride-c-n-ene (4d; the R=pH of) the R i=h. (see above) 4-phenyl-it is naphthol (' 5 gm) and

áioooi

2 it

pdietilsminofenilproparglieo

(40). (5 g) are dissolved in

olueno

(200 crude 3) and alumina (i00) was crazy

adieiona

- of the. The ReportingJBoss % of the Phew

reasão

was

aqueeida

i00° it g per minutes, cooled slightly and filtered. 0

repique

al1 pounds yne was % wool °ado with acetone and the filtrate (3x 200 em3) toluene and extra % acetone were the combined @ the solvent was removed and the residual oil cleaned by flash chromatography on alumina (400 gm) using a mixture of petroleum ether 1:3 and W, and, 60 as

elvense

, solvent was removed and the residue then carefully

oromatografia

for purifying column (200 gm) on alumina using foot

úróleo

(w, and, 40q0) as eluens % and, the fraction was evaporated and the Res.

helioorômlea

C.S. crystallize from a mixture of gasoline and 1:9

cloroformlo

(w, and, 40:60 - °0), 0

poluto

demonstrated a response

helioorIoa

clear at methodology it

azulo.æ

The

espectr

.=the habits BOI % in chloroform before and after exposure to a gun and instantaneous light is shown in Figure 8.Example 6•6 it Benzes O 2 it

me %il

it 2 p-di

ilaminobenz

% (15)

oorom

in (see above) a hot solution of pool (14) 9enan % (1.7 "gm) and alcohol 2 it DL"

etilamlnof

"

enilpr

the!(4c)

0argŒ

and I (2.5 gm) in toluene (30 em3) was poured into a dry alumina column nuts. The material was

eluhelioerômico

- {O with

olorofaínio

. solvent was

remgvido

oil

residnal

purified by

oromatograflaáoida

(75) on alumina using a solution of

iclorometano

(1:20) and petroleum as

eluan

% and. Removing the solvent left a pale yellow

õleo

that " in crystallize from

petró

OEL, gave the B

zooromeno

(15) attachable. yellow crystals

lidoso

EX-L broad, 7, .6 -. d-a-m is, % 1 - 9 -

oxlf

.m and T - cos 2-M particles is Ti-L 2&} ID is Ti, sensor "% Knob - Enzo to accelerate. (16)

oromeno

(.see above) a hot solution of 7-methoxy-4 - (-p-

metoxifauil

) - (1) of L-

nafZ.ol

(1.5 gm) and alcohol 2 p-diethylamino -

fenilpzoparg

. !(4) triton (3 gm) in toluene (30 cru3) was poured onto

oolunaàeáoido

albumin (75 gm) dry and worked up as in the previous example the

desori

%. THE:(16)

benzoormauo

was obtained

cmuo

a nearly colorless powder.

Rxemplo

8 2 me BallerupTlf .2 - 0,

Rietilaninofe

LiI L-

blsbenzocromeno

(18) - (staying above)•L., n-diisopropyl

hldrox

' % (17) by German

uaf

' (it gm) was suspended in %% and

olueno

who do (350 cru3) and p-

die %ilomlnofenilproparliQo

(4 L) (25 gm) added. Acidic alumina fibers (400 gm) was then added to the mixture (i0 min.)

aqueoi

nanodispersion with occasional % action, in a bath water, alumina and expired with IDF %

raŒa

aq8% one (2 x 200 em3).0 filtered and the WR Ill %% cleaned and-

¢aporadoe

oil al reports the mind

colmado

% residual % purified by

oromaoErafíaáoida

on alumina (i00 gm) the the column was first

aluída

with tumors that removed the main impurities

coloriŒaB

followed mixture

ane

foot

róleedielorome

% % (i: i0).The

fragãoheliocrômioa

gave a pale yellow oil which solidified to give a yellow powder

páll

. oD "II, .5 - '

bIsbenz

OCR and the %" (18).Example 9.. 6 it

cl.or

0 - 2 2' - - me-bis-Coupling TSI L. Miño-b-

enz

the Cr (22) ene (see above) ketone (19)

Nischler

(25 in - tetra-

Idrofranc

was treated one hundred

aeetile

% and and sodium (18 gm) with a suspension in xylene. The ReportingJBoss was boiled for 3% Phew wa working gave

rlnoIpal

EN is not recovered but the ketone residual oil and 4 chloro-

l.naftol

(4a) were dissolved in toluene and added to a acidic alumina column. A

azül

intense coloration was observed

q.uando

juice % forward the

raŒiaçãc

2 EU

nãõ

was given by (19) ketone and

isoheler

and 4010 rc1 it

naftc

1 (.4a) Codebook w 0 9

ndΛee

like and this s er it is likely

benzooromeno

. (22, The R=ol hydrochloride) example 2 it

me %il

it 2 it

plrrclidcnofenilben

-

corcmeno

(2d ;-consumer-H bond)

icool

-p-

pzrroli

".. r-enyl

uofopargzllee

(20) the R, (2.5 gm) and L-

naf %ol

(3 gm) were dissolved in toluene (50 ro3) and the solution passed

descendentemente

in a alumina column (150 gm) access using toluene as eluens % and.The fraction was washed with the R bring deep

elor

acid d-ECO

dilulào

cease remove impurities more basic colored, social LID

íde

•hydroxide then with AU. The solution was evaporated under pressure

toluencsecadae

Red Blue

zlda

and the residue chromatography again in

alum

'yne acidic (i00 gm) using a 5:1 Phew ReportingJBoss % of

ciclehexeno

and

diclorome

% year as elu6n % and, for the °dar

benzooromeno

(2d, - the R' hr), as a colorless oil, Ill example I! 6oloro it 2 it

me %i

, 1 it 2-O pyrrhic Sid.a Ono ERF. D. h. omen.c

enz±

. (2d; r=c1) solution and p-

pizToli8inof_

=

lpropargzlico

c20) (5 gm) and 4 it

odoro

L-

naf %ol

(5 gm) in toluene (75 cm3) was passed

descendenemen

%% and on a column of alumina weld root (i00 gm) using toluene as eluens % and. The colorless flask " of R=100' .m

helioorômica

(that tons nated blue in the exposure light of a gun light-ins NA % T-AEs) was evaporated and s @ II and residual

recrlstallzado

of acetone. The first

oul

% IVR and

¿

's % s pure was almost colorless

benzooromen

(4d;=R-LC).

Dlo

.

Exem

. 12, 2 it servile it 2 p--

Qorfol_ofe_nilbazocromeno

(3d; r=h) an alcohol solution 2 p-

morfolinoproparg

it

ílico

(3c) (3.5 gm) 1 in-immature % 01 (4 gm) in toluene (50 in 3) was passed in a

ementedescendeu

% acidic alumina column (-150 gm), using

olueno

as eluens % and %.The

cromatografirabalho

% and the rated, as above, the

benzocromeno

(3d; r=h) as colorless RO % s from chloroform and cyclohex ' ene. Sec s!the Ro qualified 0ec %% the IVO in chloroform before and after exposure to the Z-L

um.csnhinstan

%

ânea

is shown in Figure example, 6-chloro - - catch ., s , i to II•% 1 - L 2 - dL m liquid R is

ileminofenilb

%. from Enzo crom6no II (4"; the R=

cŒ

) an alcohol solution 2 p-

Œie %ilaminofanilpropargílioo

(40) - (i0 gm) and 4 it

oloro

L-

naf %ol

(i0 and) was dissolved - toluene (150 em3), heated to 809c is passed

deseendenemen

%% and in a column Alu yne acid (200 gm) using d-

olorome

% year (200 cru3) as eluens % and. The RES.. - will accelerate

helloorôeLioa

was separated and the

solven

% is removed.I00 residue was

eroma

%

oErafado

on alumina (300) the acid, using 1:9 of

miseraradŒolomue

% year•petroleum (

p.s

.as eluens 60:8090% and). The first fraction was separated and

heliocrômica

in the evaporation gave a first crop of

benzocromenc

(4d r=01).Example 14 2 it

me %il

it 2 - -, D.,

ietilaminofenilbenzocromeno

. . ($D.; R=h) a 'solution' to 1 w 001 2 2d 1 and 1% I to the Ro 0fel min. (40) GCA

lloo

(10 gm) and L-in hi. (10 g) in %

olueno

(150 Raw) were passed in a column in the alumina fibers (150 gm) hi to the working as

desorito

above gave a D

imeira

benzocrcmeno4d culture; r=h).Ill PP -

cloz

O 2 me il2 it - (

Iç

it

feniIpiperaziniIfenil

) benzofused

cromenq

(6: D.; r=01) alcohol -

fanl

"L separatory w"

eraznllfenl

•""

iproparg

' the Li "the the (60) (i0 gm) and

¿

- chloro L-

naf %ol

(gm) outside dissolved in % ol hydrochloride ene whom (200 in 5) and alumina (150" acidic gm) was

adioionada

. The grist was heated (II h in

Œe

water bath, cooled and filtered. 0 alumina waste extracted one hundred acetone (3 x 200 em3). The filtrate and extracts are combined and solvent removed and•. 0 f was

purifioado

residue by column chromatography using alumina fibers (150 gm) acidic and a

mieztx

WR ether 1:2 and

petroíeo

, as eluent. 0

benzocremeno

(6d; r=c1) that

recristalizou

from ' a mixture of petroleum ether 1:2•

medlãa

to ether evaporated and J. L.

tamau

%, pale yellow crystals

aauŒo

(6 gm, 46% yield). Their spectrum

quall

% active in chloroform before and after exposure to light and will - instantaneous is month fate in Figure 4%.And in ium 16 2.6-dimethyl-2 p-- (a b-

fenilpiperazizilfer

yl)

benzgeromen

Q water (6d; and the R=

¿

), n-

fenilpiperazinilfenilproparEí2ioo

(6) and 4-methyl-

laf %ol

(5 gm) is

diseolvido

4MU

teluene

(200 em3) and alumina (150 gm) acid was added. The mixture was

aqueoida

(I to hr) in a

bs_uho

A, cooled and filtered. Working, as above, the D

benzocromeno

(6d; r=e), pale yellow plates as (a mixture " of 1:2 and ER and petroleum (3.5 gm, 32% yield). Its qualitative

aepeetro

in chloroform before and after exposure to•J. instant light gun and•shown in

fixura

3, Si it Ill

IŒ

6 chloro-2 it methy!- .2 - - (II, 2.1. 4 - 1. and traidro2 ISO keno Income-I last

lfenil

)

benzocromeno

(for TD; - the R - BC) alcohol (II, 2.3.4 it tetrahedron it 2 it isoq1

noli

-

nll

) of Fe

llpropargllico

(7c) (3 gm) and 4-chloro L-naphthol (sec gm) were

diesolvidos

in toluene (i00 cru3) and alumina (50 gm) added acid. The mixture was " of AZ

uecida

(5 min.) 1 in a water bath, cooled and filtered the residue alumina was washed with acetone (3 x i00 em3) and the filtrate and the WR

lOex

%% XO are combined and the

solven

, can have removed under reduced pressure. The residue was fried POU II by column and acid on alumina, using

petróle.o

p.E. Ugh: 40 - 60 - °0 as eluent. The chromene derivatives was obtained as an oil (0.7 gm) pure

amarelopálido

that darkened in storage in the vehicleand II "the, example 18" repurpose " 2 it

.etil2

it 6 it

me.%

it yl-2 - -

morfolinofenilbenzoorcmene

(8d; r=e) 3

rfolinopen %in

it 3 ol (8) (7 gm) and 4-methyl L-

naf %ol

(span SG) were dissolved in-so (200 min 3) and alumina (200 gm) acidic

fõi

adioionada°. The ReportingJBoss % Phew was

aque.

it-forward (35

mln

) in a

banhoá

/the, .

resfriad

- and filters at the residue was

Cávado

with acetone (5 x 50 em3).0 filtered and the Bond % were combined at the ' the solvent.

remvldo

. The residue was

purlflcado

by column chromatography on alumina (200 gm) using ' a 1:2 mixture of petroleum ether and!

o.e,

it 40 it 60gc as effluent. The

benzocromeno

(8d; and the R=

¿

) was obtained as a pale yellow oil (2.8 gm) that pure not induced to crystallize

poãe

SARs and darkened in remained on the dark.

emç

!the

19_

6 it worse it 2 - p

d_'lm

. and % f-ene

ilamiuo

!the Cr

euqenz

lbs (19) the the above compound was prepared analogously to example knot

desari

% s " the product of this reaction shatter (5 gm) was purified by column

ouidadosasroma

%

ografia¿

U.S.S.

Œdo

neutral alumina (i00 gm) and a mixture and light petroleum ether and

oómo

eluent. (19) the

oromeno

was. obtained as colorless crystals (20 mg) that almost

coloremrapld

man % and on exposure to light. CPE blended HEU and the Ro qna3d %%% the BOI in chloroform product supplier network sites and after exposure to an d-gun "% ZZ9. nA %% ins.

âneo

is millstones % squeegee in Figure 6." The form f %

oclorldaemuaeoe

MIU % more the same as active ingredient

iŒam

% of n and Q water reads homolog 2 it

me %ila

.The

_Exem

6oloro it 2 it's always i to II - 1 - 2 AB•alkali|

œ

(alkali me I-I-I-yl %

erazini

181 LR•

Ifeni

II J. benzofused

oromeno

I to II (S.D.;=01)

Icool

alkali

me %ilpiperazinilfenilpropar

- stage (50) (3 gm) and 4-chloro L-

naftòl

(5 gm) were dissolved in %

oluançqusn

% and (3 crude 150) and acidic (i00 gm)

alumlna

was added, the mixture was heated (45

mln

) in a bath and cooled will wa

¿

AU. glacial acetic sou. (50 m3) was

adioionado

alumina and IDF. + dy and washed with a mixture of 1:19

áoidoaoet

"" in the co

aoetona

(5 x i00 as3), IP

radõ

0 1% and the plies were combined and organic solvents removed using an evaporator

roduzida

°pressío tampon rotates %

orŒo

, •hr "the residual oil was purified by column chromatography on alumina

áoiŒa

(200 gm) using a mixture 1:2 of is % er and petroleum (w" EO and 40: 60g0) as eluens % and. 0 benzofused (S.D.; the R=ol hydrochloride) was obtained shotgun a nearly colorless oil, pure, (0.3 gm), that can be induced to crystallize

nãQ

. ." Example 21

Prepa.raOão

it

Œe

2 it

me %il

it 7 it me %oxi2 p-

die %i

nofenilbenzo9romei % m is the (4d; r=h i=0 and the R) a solution of alcohol 2 p-

die %ilafenilpropemgllco

(40) the (19.5 gm 0 "05

moJ.es

) and -

me %oxi

it

lnaf %ol

(15 gm, 0.09 honey)

forar

" dissolved in toluene (250 em3) and aqueoi8os in a bath of @ to the AU. The solution % who do and was passed

desoen

ene

emen

%% and the U-alumina column (400 gm) dry acidic

eludiaolueno

% and with the % is the fluent not be more fu %

oõrômico

. Toluene was removed and the O1 or immature•

reeiduo

" MPE % the

rafado

on the Jemima acidic (300 gm) using gasoline (P.E. Ugh @ °0 - 60 - 80) and is %% and the ou eluens tumors.The solid

desoolorou

, after removal the

solven

% and, was further purified by chroma %

ografia

on alumina (150 gm) using acidic % foot

róleo

(0 6 0 - 80° from B.P.) as eluens % and.Removal of the solvent left a solid which was

reorisalizado

%% the pair go from petroleum (p°e. 60 - 80 - °0) giving the Cr Ueno's desired shotgun

oris

% s pale yellow.The absorption spectrum of the forms of the series

ooloridas

ho7% times the

matizo

depends on the nature of the powder 8ubs highlighters yn % and position 2. general ushaped HCT are blue

aazu

/!

oúrpura

.In eject Table, the invoke Ceres of the various specific given. For comparison, the compounds do not

rogênio

% Ni-are given B in Table).An EE BC yellow hr ol hydrochloride I to farm

morfoltno

hr purple-blue purple BC morpholino

loiperiaino

hr blue purple the

bensocremenos

containing•@

roge

o °, may be incorporated within the of the of the R••to co MPIs in lens PL, 9 - "" oThe, as the L 1 0 0.0 s fuh

ollcarbona

the methacrylates

alqulla

. A plastic lens material commercially known as RO 9 is the material more

comumen

% is used for lens making and Romanians

hellooFom_ioosdescri

% the UR-and the

ioodem

be

inoorporados

lens Regally formed

abrioadas

L R-Art.

dèste

material by impregnation.Impregnating paean be conducted RO dipping into a solution of compound

helioorômlco

. Solvents laughed•fates are

preá

•

fidos

because they are inert and have a raises the point El li9eo.

7mersão

in solution %

v.r

LA of independently as in the solvent•

heliocrômico

reflux is a convenient procedure, preferred solvents are the range L of solvents and perfluoro Partner bicarbonate. the dihydroxy

ponívais

8 ghm Ajuda and the range I to similar fluorinated solvents IDS 100 8 of the alkali invisible is0

ChemioalsLimi

DE %.Lenses having the eager to brown coloration in UV light may be made of AMEn % 0r bring the of the pre -

iamen

SE legen %% %•rooms and is

simulane

mind or sequentially with

acosto

he3_ioorômioo yellow color and with a•••placed blue color, RO example the

ceml

the % of the

exem

it 6 the applicant's copending application g3 8611837 was dissolved in a solvent available from the iperf

perfluora

0 7 under the tradename L. c40 (E 16500) to form U to saturated solution and a lens made of plastic 10art ± r 0r39 fo-alkali solution immersed pounds reflux for 30

mln

. The lens was then dipped into a solution of the compound described in example 1 of this report for 30 min. under similar conditions. The resulting lenses colored for

marrem

8ubme were then had to a lamp of i000

aimilando

watt solar radiation.Bud an alternative to solution dip DOE at

heliocrômlcoe

compounds, the unpredictable

¿

Freemason can be effected RO exposure of lenses to steam of compound

helioerômico

. This may be

obtidõ

, pain example, heating the compound

heliocrômico

in a vacuum chamber in P are here of a lens to be treated. Heating at a

temleratu

Ra of about 160 - °0 by about I h under a vacuum below about the, 25 10mbar, resulted in

Œentescoloriamexpoalção

in that the UV light

impreé

N.A.•0 effect. tion is enhanced by pre-treatment of plastic lens dip in %

etraldrofurano

at reflux for one hour.

Os.espeotros

accompanying absorption (Figures I to 8) illustrate

fotoerômicas

properties - accordingto "Z-" s of D.

heliocr

compounds "

ioos

blue color of this, invention in all balance cases, the within curve represents the subject compound" in its colorless state and the upper curve after

expoaiçao

to ' light gun launched

antânea

%. Compared with

oomposbosò.e

spiro-adamantane descriptor " in the 'wa'

ò.ente

dependent on applicant Technique 86

I1837

, compounds of this invention strongly absorb Z-in '

egião

of 5 to 600 min. With reference e.g.

finara

II " to within curve represents the compound in its colorless state and the sleeve curve. top after irradiation with a Z-simulating sun lamp. Figure 2

mcgtra

behavior of this brr -

oromeno

Example 8. again " the lower curve represents the compound uncolored state and the upper curve the colored state. An important advantage is the fact that the state of this compound absorbs over colored

ne.o

strongly than UV-colored state in the region. As a consequence, if has the effect of reduced inner filter and a higher conversion of the material W to give a colored state uponirradiation.Despite the impregnation solutions from the solvents are required be the annual process of incorporation were combined with preferred mind

helierômlcos

compound in plastic material, such as GE 39, is also

põssível

impregnate the

eompostoe

" from a fusion.In order to test for impregnating

ioor

Kon % act from melting as II art possible, the

amõstr

the

eomposto

Example 4 was cast onto a plastic sheet and a RO 39 if&MOA RO

dlcionada

sheet 39 to form a rum sandwich. The sample was maintained at 160 0 for 40

mlmutostresfrlaça

then, and the washed w chloroform

expeotro

of predictable of CR 39 demonstrates a 'DOC' impregnated of 25 "7 x 10 - 5 mere ERA

impreEnação

in a sides this is' compares one hundred a, 0od, of 19, 3 x 10-5}

¿

in obtained when the ME the

cempos

% the was impregnated in milliamps sheet RO 39 pair % IR of a solution of solvent FL.

orcarbono

fc40 deals bonded by 3 I colored"

oratlon

.•0 term '0od' relates the % ACL

¿

density material in the form colored unpredictable

¿

swim.' * When s " incorporate

heliocrômicos

compound on the materials of plastic is padding is the pair go % melting, pose'S % prior to exclude oxygen in order to prevent degradation of the compound

heliocr

goeldi.the Ro 0u % 9ara process incorporate

õsheliocrômicos

compounds in the WR %% inc. plastic involves include the composed in milliamps

erlal

%% 6 1 0% of plastic pair going from which the legen % # and is molded. the %%%

descrlecnŒca

••is in the ene %% paddle and US pneumovirus ns MD 4576766° although invention has been described with reference

partleular

use from GE as

eompostcs

'

heliocrômimos

ERA manufacturing

àe

hurt %%% s f

oreaivam

, will be on the % o that the

oompos

% the also has other uses deriving their PTS

riedad

sec f % $SAC the OCR. 0 placed flanges e.g. be used w held up generally, IDF % ROIs and variable density.I. think Separation %

álmlca

or planar deepening in light sol and converts to a pale or colorless condition in white light in % in!as RAE

oera

% environments in U-s, the air and the ut % link % tumors that fact at the R same incorporated " or coated'S. at least two EHB'S Principal

oompos

% XO

hellocromloos

" one of the

referidoe

compound comprising a spiro-

benzoplrauo

or

espironaftopiranõ

of

adaman

% year that a group ad8man % year s % presence i0 at position 2 it spiro ring or SLS

benzopiraiuoopirano

and a BSE compound comprising a static

benzoou

naphtho go the % between a inc. of I %% Ni-

u_inçe

consented

rogênio

at position 2 of the ring tyrant.2. lens and accordance with claim II, wherein the AF

pelao

% d that a (referred to compose them -% the his

ocrômioo

is a

piraneesplronafJ

AD Mann % year and a second compound in the general formula

ocromlco

Hell