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Синтез метил сульфона /2-аминофенил/

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Ainoaea?noaaiiue eiieoao ?O ii aunoaio ia?aciaaieth

?inneeneee Oeieei Oaoiieiae/aneee Oieaa?neoao

eiaie Ae.E. Iaiaeaeaaaa

Eaoaae?a oeiee e oaoiieiaee i?aaie/aneeo e?aneoaeae

O/aaiay iao/ii-enneaaeiaaoaeueneay ?aaioa ii oaia:

Iieo/aiea iaoee [2-aieiioaiee] noeueoiia

Nooaeaioa VI eo?na

Iaeneiiaa I.A.

Iao/iue ?oeiaiaeeoaeue

aeioe. AEaeoia A.ss.

Iineaa 1998

Iaeaaeaiea

TOC \f \t “Caaieiaie 2;1;Caaieiaie
3;2”

Iaeaaeaiea GOTOBUTTON _Toc431546517 PAGEREF _Toc431546517 2

1. Aaaaeaiea GOTOBUTTON _Toc431546518 PAGEREF _Toc431546518 3

2. Iauay /anoue GOTOBUTTON _Toc431546519 PAGEREF _Toc431546519 4

2.1 Noaia neioaca GOTOBUTTON _Toc431546520 PAGEREF _Toc431546520 4

2.2 2,2’-aeeieo?iaeeoaieeaeenoeueoeae GOTOBUTTON _Toc431546521
PAGEREF _Toc431546521 4

2.3 2-ieo?ioeioaiie GOTOBUTTON _Toc431546522 PAGEREF _Toc431546522
5

2.4 Iaoee [2-ieo?ioaiee] noeueoeae, i-ieo?ioeiaiecie. GOTOBUTTON
_Toc431546523 PAGEREF _Toc431546523 5

2.5 Iaoee [2-ieo?ioaiee] noeueoii GOTOBUTTON _Toc431546524 PAGEREF
_Toc431546524 6

2.6 Iaoee [2-aieiioaiee] noeueoii GOTOBUTTON _Toc431546525 PAGEREF
_Toc431546525 6

3. Yenia?eiaioaeueiay /anoue GOTOBUTTON _Toc431546526 PAGEREF
_Toc431546526 7

3.1 2,2’-aeeieo?iaeeoaieeaeenoeueoeae (2) GOTOBUTTON _Toc431546527
PAGEREF _Toc431546527 7

3.2 2-ieo?ioeioaiie (3) GOTOBUTTON _Toc431546528 PAGEREF
_Toc431546528 7

3.3 Iaoee[2-ieo?ioaiee]noeueoeae, 2-ieo?ioeiaiecie (4) GOTOBUTTON
_Toc431546529 PAGEREF _Toc431546529 7

3.4 iaoee [2-ieo?ioaiee] noeueoii (5) GOTOBUTTON _Toc431546530
PAGEREF _Toc431546530 8

3.5 iaoee [2-aieiioaiee] noeueoii (6) GOTOBUTTON _Toc431546531
PAGEREF _Toc431546531 8

4. Auaiaeu GOTOBUTTON _Toc431546532 PAGEREF _Toc431546532 8

5 Eeoa?aoo?a GOTOBUTTON _Toc431546533 PAGEREF _Toc431546533 9

6 I?eeiaeaiey GOTOBUTTON _Toc431546534 PAGEREF _Toc431546534
Ioeaea! Caeeaaeea ia ii?aaeaeaia.

1. Aaaaeaiea

Oeaeueth aeaiiie ?aaiou yaeyaony iieo/aiea oeaeaaiai i?iaeoeoa – iaoee
[2-aieii-oaiee] noeueoiia, eioi?ue iiaeao auoue eniieueciaai a ea/anoaa
enoiaeiiai niaaeeiaiey a neioaca acie?aneoaeae.

Ia eaoaae?a i?iaiaeeeenue ?aaiou ni noiaeiuie aauanoaaie, iai?eia?
iieo/aiea N,N-aeeiaoeeaieaea e N,N-aeeyoeeaieaea i?oaieeiaie eeneiou
enoiaey ec 2-oei?ieo?iaaiciea, /a?ac aeenoeueoeae, n aeaeueiaeoei
enneaaeiaaieai eeiaoeee acini/aoaiey N,N-aeeaeeeeaieaeia i?oaieeiaie
eeneiou n N-aoeaoee-E-eeneioie i?iaiaeeeinue Nie?iiaie O.

2. Iauay /anoue

2.1 Noaia neioaca

A ?acoeueoaoa aiaeeca iao/iie eeoa?aoo?u, i?eaaaeaiiie a ?acaeaea 5, ia
iniiaaiee aeinooiiinoe enoiaeiuo ?aaaaioia e i?inoiou iaoiaeeee aue
aua?ai neaaeothuee iooue neioaca iaoee-[2-aieiioaiee]-noeueoiia:

2.2 2,2’-aeeieo?iaeeoaieeaeenoeueoeae

Ia?aui yoaiii iaoae ?aaiou auei iieo/aiea
2,2’-aeeieo?iaeeoaieeaeenoeueoeaea. A eeoa?aoo?a [1] aeinoaoi/ii
iiae?iaii iienai iaoiae aai iieo/aiey.

I?e niaoaiee eeiyuaai ?anoai?a 2-oei?ieo?iaaiciea (1) a nie?oa ni
nie?oiaui ?anoai?ii aeenoeueoeaea iao?ey iieo/eee
2,2’-aeeieo?iaeeoaieeaeenoeueoeae (2), eioi?ue i/enoeee io
iai?aaie/aneeo nieae, enoiaeiiai aauanoaa e iiai/ii ia?acothuaainy
i-oei?aieeeia, iineaaeiaaoaeueii i?iiuaay aiaeie, nie?oii e ?acaaaeaiiie
nieyiie eeneioie. Auaeaeaiiue i?iaeoeo aeaeoiai oeaaoa
ia?ae?enoaeeeciauaatho ec eaaeyiie oenoniie eeneiou.

Iieo/aiiue n auoiaeii 40% aeeieo?iaeenoeueoeae i?aaenoaaeye niaie
o?iiaoia?aoe/anee eiaeeaeaeoaeueiia aauanoai n o. ie., niioaaonoaothuae
eeoa?aoo?iui aeaiiui [1] e [2]. Ec yoiai iiuoa auei auyaeaii, /oi ia
auoiae i?iaeoeoa ieacuaaao aieueoia aeeyiea /enoioa aeenoeueoeaea
iao?ey. Oae i?e ia?aoiaea ia aeenoeueoeae iao?ey ec ae?oaie /enoiou,
?aaeoeeiiiay ianna, i?e aeiaaaeaiee e nie?oiaiio ?anoai?o
ieo?ioei?aaiciea iieo/aiiiai ?anoai?a noeueoeaea, i?eia?aoaea /a?iue
oeaao, a ioee/ee io e?aniiaaoi-ei?e/iaaiai a neo/aa n aieaa /enoui
aeenoeueoeaeii. Oaeaea oaaee/eaaeinue niaea?aeaiea oeioaiiea a
?aaeoeeiiiie niane (iiyaeyeny oa?aeoa?iue caiao). Aeey auaeaeaiey
i?iaeoeoa (2) i?eoiaeeeinue iaaeeaiii i?e ia?aiaoeaaiee aeiaaaeyoue
?anoai? ia?aeene aiaei?iaea, eiio?iee?oy i?ioeann ii oeaaoo e
iaoaie/aneei oa?aeoa?enoeeai ?aaeoeeiiiie niane: oeaao ?anoai?a e?aniue,
i?iaeoeo a aeaea iaeeeo aeaeouo /anoe/ae.

2.3 2-ieo?ioeioaiie

A eco/aiiie eeoa?aoo?a anoue ?acee/iua iaoiaeeee neioaca aeaiiiai
niaaeeiaiey. Iai?eia? a aeenna?oaoeee [2] e noaouea [3] i?eaaaeai iaoiae
iieo/aiey 2-ieo?ioeioaiiea ec 2,2’-aeeieo?iaeeoaieeaeenoeueoeaea n
eniieueciaaieai nie?oiaiai ?anoai?a aeenoeueoeaea iao?ey. I/enoea
ia?ae?enoaeeecaoeeae ec oenoniie eeneiou. Auoiae ii aeaiiie iaoiaeeea
iieo/eeny iacia/eoaeueiue, aiciiaeii ec-ca iaaeinoaoi/iie /enoiou
aeenoeueoeaea iao?ey. A ?aaioa [6] a ea/anoaa ainnoaiaaeeaathuaai aaaioa
i?aaeeaaaaony eniieueciaaoue aeae?inoeueoeae iao?ey. A noaoueyo [4] e
[5] iienaiu iaoiaeu n eniieueciaaieai noeueoeaea iao?ey e aeae?ieneaea
iao?ey a aiaeii-nie?oiaie n?aaea i?e eeiaiee. I?e/ai a noaouea [5]
2-ieo?ioeioaiie iaoeee?otho aac auaeaeaiey.

Iu i?iaiaeeee ainnoaiiaeaiea iieo/aiiiai a i?aaeuaeouai iiuoa
aeeieo?iaeeoaieeaeenoeueoeaea ii iaoiaeeea, iienaiiie a noaoueyo [4] e
[5]. E eeiyuaio nie?oiaiio ?anoai?o (2) i?eaaaeytho aiaeiue ?anoai?
aeenoeueoeaea iao?ey e aeae?ieneaea iao?ey, iinea /aai ?aaeoeeiiioth
ianno, ie?aneaoothny a /a?iue oeaao auaea?aeeaatho i?e eeiaiee, a caoai
a aeanyoue ?ac ?acaaaeytho oieiaeiie aiaeie.

A ?acoeueoaoa na?ee iiuoia auei auyaeaii, /oi neeueiia aeeyiea ia auoiae
i?iaeoeoa (3) ieacuaatho /enoioa aeenoeueoeaea iao?ey, a?aiy eiioaeoa n
aoiinoa?ie, nei?inoue iiaeeeneaiey ?anoai?a ieo?ioeioaiieyoa. I?e
i?iaaaeaiee ?aaiou a i?aaeuaeouai naiano?a eiaiii yoa noaaeey aucaaea
iaeaieueoea cao?oaeiaiey. A eoiaa ?acee/iua oaeoi?u, iaoathuea
iieo/aieth oeaeaaiai i?iaeoeoa auee o/oaiu e i?iaeoeo auaeaeai. Iinea
oeeueo?aoeee aeanyoee?aoii ?acaaaeaiiiai ?anoai?a ieo?ioeioaiieyoa
iao?ey io iai?i?aaae?iaaaoaai aeenoeueoeaea (2), i?e/ai, aaeaeo oiai,
/oi, aeaaiaea?y iaeiio ?acia?o /anoeoe aeenoeueoeaea, oeeueo? auno?i
caaeaaeny, aai i?eoiaeeeinue iaiyoue 2-3 ?aca ca a?aiy oeeueo?aoeee,
oeeueo?ao iaaeeaiii ?acaaaeytho i?e ia?aiaoeaaiee nieyiie eeneioie, i?e
yoii auiaaeatho aeaeoi-?uaeea /anoe/ee ieo?ioeioaiiea, a ?anoai? iaiyao
oeaao n oaiii-aeoiaaiai ia y?ei aeaeoue. Iinea yoiai nenoaia aeey
ia?aciaaiey /anoeoe aieaa e?oiiiai ?acia?a aeatho iaiiiai ionoiyoueny, e
oeeueo?otho. Iieo/aiiue iinea oeeueo?aoeee oeioaiie
ia?ae?enoaeeeciauaatho ec nie?oa e eeai n?aco iaoeee?otho, eeai nooao a
aaeooi yeneeaoi?a iaae uaei/ueth. Ai aoi?ii neo/aa ia?aae iaoeee?iaaieai
ieo?ioeioaiie (3) ia?aaiaeyo a uaei/iie ?anoai? e iooeeueo?iauaatho
aeeieo?iaeenoeueoeae (2).

Auoiae ieo?ioeioaiiea iinea ia?ae?enoaeeecaoeee ninoaaee 38%. Ia
o?iiaoia?aiia iaia?oaeaiu neaaeu aeeieo?iaeenoeueoeaea, aiciiaeii ca
n/ao ieeneaiey ?anoai?a oeioaiiea ia o?iiaoia?aoe/aneie ieanoeiea. O.
ie. niioaaonoaoao iienaiiie a eeoa?aoo?a [2], [3], [4].

2.4 Iaoee [2-ieo?ioaiee] noeueoeae, i-ieo?ioeiaiecie.

Ai anao ec eco/aiiuo iaoiaeee i-ieo?ioeiaiecie (4) iieo/aee
iaoeee?iaaieai 2-ieo?ioeioaiiea (3). ?acee/ea a iaoeee?othueo aaaioao. A
noaouea [4] eniieueciaaeny eiaeenoue iaoee a uaei/iie aiaeii-nie?oiaie
n?aaea. A noaoueyo [5] e [6] a ea/anoaa iaoeee?othuaai aaaioa
eniieueciaaeny aeeiaoeenoeueoao, nouanoaaiii aieaa aeaoaaue /ai
iaoeeeiaeeae. Ai anao noaoueyo n?aaea uaei/iay.

E uaei/iiio ?anoai?o ieo?ioeioaiiea (3) /a?ac iaaeeaiii i?eaaaeytho
ecauoi/iia eiee/anoai aeeiaoeenoeueoaoa. I?e yoii ?anoai? ec oaiii
aeoiaaiai iinoaiaiii i?aa?auaaony a i?ic?a/ii aeaeoue. Auiaaeatho
aeaeoua /anoe/ee ieo?ioeiaieciea (4).Eo iooeeueo?iauaatho, i?iiuaatho
aiaeie e aunooeaatho. Iinea ia?ae?enoaeeecaoeee ec nie?oa auoiae
o?iiaoia?aoe/anee eiaeeaeaeoaeueiiai i?iaeoeoa ninoaaee 50% a aeaea
naaoei-aeaeouo ieanoeiie. Oaiia?aoo?a ieaaeaiey niioaaonoaoao
eeoa?aoo?iui enoi/ieeai [3], [4], [7].

2.5 Iaoee [2-ieo?ioaiee] noeueoii

Aeaiiia niaaeeiaiea iieo/atho ieeneaieai iaoee [2-ieo?ioaiee] noeueoeaea
(4) a aiaeiie n?aaea. A ea/anoaa ieeneeoaey a noaouea [4] aua?aia nianue
o?iiiaie e oenoniie eeneio. A noaouea [5] i?aaeeiaeai iaoiae ieeneaiey
ia?aeenueth aiaei?iaea a n?aaea eaaeyiie oenoniie eeneiou. A iaieo
neo/ayo i/enoea ia?ae?enoaeeecaoeeae ec niane nie?o-aiaea.

E ?anoai?o ieo?ioeiaieciea (4) a eaaeyiie oenoniie eeneioa, iaa?aoiio ia
eeiyuae aiaeyiie aaia, i?eeeaath ii eaieyi ?anoai? ia?aeene aiaei?iaea.
Caoai i?iaeieaeatho iaa?aa i?e yoie oaiia?aoo?a. *a?ac ia?o /ania
ioeaaeaeatho, ?acaaaeytho aiaeie e iooeeueo?iauaatho iaoee
[2-ieo?ioaiee] noeueoii (5). Neaaeoao ioiaoeoue iaaeeaiioth nei?inoue
i?eaaaeaiey ia?aeene aiaei?iaea, oae aea eae e oi, /oi naia ia?aeenue
aeieaeia auoue a iaiaoiaeeiii eiee/anoaa. A ia?aue ?ac auei aeiaaaeaii
iiiai ia?aeene, i?e/ai iaonoaiiaeaiiiai ninoaaa, /oi i?eaaei e aua?ino
/anoe ?aaeoeeiiiie iannu, a oaeaea e aa iaaeiieeneaieth. Ai aoi?ii
neo/aa auee o/oaiu ioeaee ia?aie iiiuoee e ia?aeenue aeiaaaeyeanue /a?ac
eaiaeueioth ai?iieo ii eaieyi.

Auoiae o?iiaoia?aoe/anee eiaeeaeaeoaeueiiai i?iaeoeoa iinea
ia?ae?enoaeeecaoeee ec niane nie?o-aiaea ninoaaee 48% a aeaea aaeuo
e?enoaeeia. Oaiia?aoo?a ieaaeaiey niioaaonoaoao eeoa?aoo?iui enoi/ieeai
[3], [4], [7].

2.6 Iaoee [2-aieiioaiee] noeueoii

Eiia/iia aauanoai iieo/atho ainnoaiiaeaieai iaoee [2-ieo?ioaiee]
noeueoiia. A noaouea [7] i?eaiaeyony iaoiaeu ainnoaiiaeaiey oeeieii a
na?iie eeneioa ?acee/iie eiioeaio?aoeee. A ?aaioa [4] i?aaeeiaeai iaoiae
ainnoaiiaeaiey aeaeaciui ii?ioeii a aiaeiie n?aaea a i?enoonoaee
oenoniie eeneiou. Iinea ainnoaiiaeaiey iiaeuaea/eaatho, oeeueo?otho e
yeno?aae?otho aaiceiii. Caoai yeno?aaaio ioaiiytho, a aauanoai
ia?ae?enoaeeeciauaatho ec aiaeu. A ?aaioa [5] ainnoaiiaeaiea aaaeoo
aeaeaciuie no?oaeeaie a 50% yoaiiea n aeiaaaeaieai nieyiie eeneiou a
oa/aiee 24 /ania, iinea /aai oeeueo?otho, oia?eaatho, yeno?aae?otho
oei?ioi?iii e ia?ae?enoaeeeciauaatho ec iao?ieaeueiiai yoe?a.

A ?acoeueoaoa aiaeeca ?acee/iuo iaoiaeee aue aua?ai iaoiae
ainnoaiiaeaiey ieo?ia?oiiu aeaeacii a n?aaea yeaeo?ieeoa. E aeaeaciiio
ii?ioeo, i?io?aaeaiiiio nieyiie eeneioie aeiaaaeytho nie?oiaie ?anoai?
iaoee [2-ieo?ioaiee] noeueoiia (5). Nianue ia?aiaoeaatho i?e iaa?aaaiee
ieiei 8 /ania, caoai oeeueo?otho, oeeueo?ao oia?eaatho, caoai inaaeie e
oia?aiiia aauanoai yeno?aae?otho oei?ioi?iii, eioi?ue a iineaaenoaee
ioaiiytho. Iieo/aiioth iinea yeno?aeoeee ianeyienooth ianno
ia?ae?enoaeeeciauaatho ec iao?ieaeueiiai yoe?a. Ia o?iiaoia?aiia ii ieii
iyoia iniiaiiai aauanoaa, iaia?oaeaii aua aeaa iyoia. I?e iaeo?eaaiee
ieanoeiee ieneaeii acioa n iineaaeothuei ni/aoaieai n (-iaooieii
i?iyaeyaony eioaineaiay e?aniay ie?anea o iyoia iniiaiiai aauanoaa e
neaaay ie?anea o iyoai iiai/iuo i?iaeoeoia. Aiciiaeii, iiai/iua aauanoaa
anoue i?iaeoeou ieeneaiey oeaeaaiai aieia.

Auoiae iinea ia?ae?enoaeeecaoeee ec iao?ieaeueiiai yoe?a ninoaaee 27%.
Oaiia?aoo?a ieaaeaiey ioee/aaony io eeoa?aoo?iie. Oae a [6] oeacuaaaony
o. ie. 90-92 (N, a [7] 65-66(N, a [4] 53,5-54,5 (N. A iaoai neo/aa
iieo/aiiia aauanoai ieaaeony i?e 73-78 (N.

3. Yenia?eiaioaeueiay /anoue

Yeaeo?iiiua niaeo?u iiaeiuaiey anao niaaeeiaiee ?aaeno?e?iaaee ia
niaeo?ioioiiao?a “Specord M400” (Karl Zeiss Jena). Eio?ae?aniua niaeo?u
iiaeiuaiey niaaeeiaiee ?aaeno?e?iaaee ia niaeo?ioioiiao?a “Specord M80”
(Karl Zeiss Jena) a aacaeeiiaii ianea.

3.1 2,2’-aeeieo?iaeeoaieeaeenoeueoeae (2)

A e?oaeiaeiiioth eieao aianoeiinoueth 300 ie, niaaaeaiioth ia?aoiui
oieiaeeeueieeii, iiiauatho 36 a (0.15 iieue) e?enoaeee/aneiai
aeenoeueoeaea iao?ey ( Na2S(9H2O) e 150 ie 95(-ai yoeeiaiai nie?oa.
Nianue iaa?aaatho ia aiaeyiie aaia aei ?anoai?aiey noeueoeaea iao?ey.
Caoai aeiaaaeytho 4.8 a (0.15 iieue) ii?ioeiia?aciie na?u e iaa?aaaiea
i?iaeieaeatho aei aa ?anoai?aiey, i?e yoii ia?acoaony ao?iaaoi-e?aniue
?anoai? aeenoeueoeaea iao?ey. Iinea yoiai a e?oaeiaeiiiie eieaa
aianoeiinoueth 500 ie, niaaaeaiiie ia?aoiui oieiaeeeueieeii,
i?eaioiaeytho ?anoai? 31.5 a (0.20 iieue) 2-oei?ieo?iaaiciea a 50 ie
95(-ai yoeeiaiai nie?oa. E yoiio ?anoai?o iaaeeaiii i?eeeaatho ai?y/ee
?anoai? aeenoeueoeaea iao?ey. Iiea ?aaeoeey eaeao ao?ii, i?eaaaeaiea
aeenoeueoeaea aaaeoo iaaeeaiii. Eiaaea aanue aeenoeueoeae i?eaaaeai
nianue iaa?aaatho a oa/aiee aeaoo /ania ia aiaeyiie aaia, iiaeaea?aeeaay
neaaia eeiaiea ?aaeoeeiiiie niane. Caoai niaea?aeeiia eieau ioeaaeaeatho
aei 20(N, inaaeie iooeeueo?iauaatho, i?iiuaatho ianeieueei ?ac aiaeie
aeey oaeaeaiey NaCl, iaeei ?ac 20 ie yoeeiaiai nie?oa aeey oaeaeaiey
iai?i?aaae?iaaaoaai 2-oei?ieo?iaaiciea e iaeei ?ac 20 ie ?acaaaeaiiie
nieyiie eeneiou, ioaeeiatho ia oeeueo?a e aunooeaatho a aaeooi
yeneeaoi?a iaae NaOH.

Ii yoie iaoiaeeea ec 210 a ieo?ioei?aaiciea iieo/aii 105 a i?iaeoeoa.
Iinea ia?ae?enoaeeecaoeee ec eaaeyiie oenoniie eeneiou auoiae
2,2’-aeeieo?iaeeoaieeaeenoeueoeaea ninoaaeyao 84,2 a (41%). Rf 0.75
(aaicie). O. ie. 194-197 (N. Eeo o. ie. 198-199 (N [1].

3.2 2-ieo?ioeioaiie (3)

E eeiyuae noniaicee 25 a (0,081 iieue)
2,2’-aeeieo?iaeeoaieeaeenoeueoeaea a 100 ie nie?oa aeiaaaeytho aiaeiue
?anoai? 10 a (0,041 iieue) aiaeiiai noeueoeaea iao?ey e 7 a (0,175
iieue) aeae?ieneaea iao?ey, ia?aiaoeaay i?e eeiaiee 20 iei. Caoai
?anoai? aueeaatho a 1 eeo? oieiaeiie aeenoeeee?iaaiiie aiaeu e
oeeueo?otho. Oeeueo?ao iaaeeaiii i?e iiiaoeaaiee iiaeeeneytho 65 ie
eiioeaio?e?iaaiiie nieyiie eeneiou (?anoai? ec e?anii-ei?e/iaaiai
i?aa?auaaony a aeaeoue), aeatho /ooue-/ooue ionoiyoueny e
iooeeueo?iauaatho aeinooa auiaaoee 2-ieo?ioeioaiie e n?aco aunooeaatho a
aaeooi yeneeaoi?a n NaOH.

Ii yoie iaoiaeeea ec 52,3 a aeeieo?iaeeoaieeaeenoeueoeaea (2) auei
iieo/aii 22,3 a (3) Iinea ia?ae?enoaeeecaoeee ec nie?oa auoiae 20,1 a
(38%). O. ie. 57-59(N. Eeo o. ie. 58(N [3], 57-58(N [4]. Rf 0,7
yethaio oei?ioi?i : aaenai 1:1.

3.3 Iaoee[2-ieo?ioaiee]noeueoeae, 2-ieo?ioeiaiecie (4)

A e?oaeiaeiiiie eieaa n ia?aoiui oieiaeeeueieeii aioiayo ?anoai? 20 a
(0,129 iieue) 2-ieo?ioeioaiiea, 15 a (0,375 iieue) aeae?ieneaea iao?ey a
100 ie aiaeu e iaa?aaatho aai aei 50(N. E iieo/aiiiio ?anoai?o iaaeeaiii
i?eaaaeytho /a?ac eaiaeueiua ai?iiee 40 ie (d 1,35 a/ie, 54 a, 0,42
iieue) aeeiaoeenoeueoaoa e 10 a (0,25 iieue) aeae?ieneaea iao?ey. Iinea
i?eaaaeaiey ia?aiaoeaatho 30 iei. A yoi a?aiy ?anoai? iaiyao oeaao n
oaiii aeoiaaiai ia i?ic?a/ii-aeaeoue. Iooeeueo?iauaatho auiaaoee
2-ieo?ioeiaiecie.

Iieo/atho 13 a (60%) Iinea ia?ae?enoaeeecaoeee ec niane nie?o-aiaea
auoiae 12,4 a O. ie. 59-61(N. Eeo o. ie. 92-94(N [6], 59-60(N [4]
58-60(N [7], 61,5-62(N [5]. Rf 0.6 yethaio oei?ioi?i : aaenai 1:1.

3.4 iaoee [2-ieo?ioaiee] noeueoii (5)

A e?oaeiaeiiiie eieaa ia 200 ie iaa?aaatho aei eeiaiey ?anoai? 7,5 a
(0,044 iieue) 2-ieo?ioeiaieciea a 50 ie eaaeyiie oenoniie eeneiou. Iinea
yoiai e iaio iaaeeaiii, /a?ac eaiaeueioth ai?iieo, aeiaaaeytho 20 ie 30%
ia?aeene aiaei?iaea. Caoai ?anoai? iaa?aaatho a oa/aiee aeaoo /ania ia
aiaeyiie aaia. Iinea ioeaaeaeaiey e ?acaaaeaiey 75 ie aiaeu ioaeaeyaony
iaoee [2-ieo?ioaiee] noeueoii a aeaea aaeuo e?enoaeeia. Eo
iooeeueo?iauaatho, i?iiuaatho aiaeie e aunooeaatho.

Iinea ia?ae?enoaeeecaoeee ec niane nie?o-aiaea auoiae 4,7 a (48%) O. ie.
104-106(N Eeo. o. ie. 105-106(N [7], 104-105(N [4], 105-106(N [5].

Rf 0,3 yethaio oei?ioi?i : aaenai 1:1.

3.5 iaoee [2-aieiioaiee] noeueoii (6)

Ia?aae ainnoaiiaeaieai 6 a aeaeaciiai ii?ioea i?io?aaeytho ?anoai?ii 1
ie (0.032 iieue) 35%-iie nieyiie eeneiou a 10 ie aiaeu i?e 5-oe ieiooiii
eeiy/aiee. Caoai i?eaaaeytho ?anoai? 4,5 a (0,0225 iieue) iaoee
[2-ieo?ioaiee] noeueoiia a 115 ie 50% yoaiiea. Iinea i?eaaaeaiey anaai
?anoai?a ieo?iniaaeeiaiey ?aaeoeeiiioth ianno iaa?aaatho au? 8 /ania.
Caoai ioeaaeaeatho aei eiiiaoiie oaiia?aoo?u, aeiaaaeytho 2 a
eaeueoeeie?iaaiiie niaeu e 25 ie yoaiiea. ?aaeoeeiiioth nianue
iaa?aaatho e iooeeueo?iauaatho io aeaeaciiai oeaia, eioi?ue
yeno?aae?otho oei?ioi?iii. Oeeueo?ao oia?eaatho, ianuuatho iiaa?aiiie
nieueth e yeno?aae?otho oei?ioi?iii. Yeno?aeou iauaaeeiytho, inooatho
aacaiaeiui noeueoaoii iaaiey, oeeueo?otho e ioaiiytho oei?ioi?i ia
?ioi?iii enia?eoaea. Iieo/eaoaany ei?e/iaaia ianei ia?ae?enoaeeecotho ec
iao?ieaeueiiai yoe?a.

Auoiae 1 a n o. ie. 73-78 (N. Eeo O. ie.: 90-92(N [7], 53.5-54.5(N [5],
65-66(N [6].

Rf 0,7 yethaio – oei?ioi?i. Iiai/ii iieo/aiu aua 2 iyoia n Rf 0,15 e
0,25 niioaaonoaaiii.

4. Auaiaeu

Eco/aia e io?aaioaia noaia iieo/aiey iaoee [2-ieo?ioaiee] noeueoiia ec
i-ieo?ioei?aaiciea.

Auyaeaii, /oi a aeaiiie noaia neioaca neeueiia aeeyiea ieacuaaao /enoioa
?aaaaioia.

I?e iieo/aiee iaoee [2-aieiioaiee] noeueoiia iaia?oaeaiu iiai/iua
i?iaeoeou, aeathuea ie?aneo i?e aeeacioe?iaaiee e ni/aoaiee n
(-iaooieii.

5 Eeoa?aoo?a

Neioacu i?aaie/aneeo i?aia?aoia na.1 n. 49.

O.A.*eaeniaa. Neioac e OO-niaeo?u iiaeiuaiey ianeiiao?e/iuo
aeeoaieeaeenoeueoeaeia. Aeenna?oaoeey ia nieneaiea o/aiie noaiaie
eaiaeeaeaoa oeie/aneeo iaoe.// I. 1971. 161n.

A.Chrzaszczewska, B.Bielawski, Lodz. Towarz. Nauk, Wydzial III, Acta
chim., 1958, vol 3, p. 87.

D.G.Foster, E.E.Raid. The influence of sulfur on the color of azo dyes
further investigations.// The Jornal of the American Chemical Society,
1924, vol 46, p.1936-1948.

M.P.Cava, C.E.Blake. // The Jornal of the American Chemical Society,
1956, vol 78, p.5444-5446.

K.Brand. // Berichte, 1909, vol. 42, p. 3465.

F.Claasz. // Berichte, 1912, vol. 45, p.1022-1030.

PAGE 2

PAGE 10

i = 210 a

23%i

i = 1 a

(oei?ioi?i)

Rf=0.7

Tie 73-78

48 %i

i = 4.7 a

aaenai)

(oei?ioi?i-

Rf=0.3

Tie 104-106

50 %i

i = 12,4 a

aaenai)

(oei?ioi?i-

Rf = 0,6

Tie 59-61

38%i

i = 20,1 a

aaenai)

(oei?ioi?i-

Rf = 0,7

Tie 57-59

40 %i

i = 82,3 a

(aaicie)

Rf = 0,7

Tie 194-197

l

C

H

e

F

2

H

N

3

H

C

2

O

S

4

O

S

2

)

3

H

C

(

H

O

a

N

S

2

a

+ N

H

O

a

N

H

O

5

H

2

C

2

S

2

a

N

2

O

N

3

H

C

2

O

S

2

O

2

H

H

O

O

C

3

H

C

2

O

N

3

H

C

S

2

O

N

H

S

2

O

N

S

S

2

O

N

l

C

2

O

N

Noaia neioaca iaoee [2-aieiioaiee] noeueoiia

(2)

(1)

(6)

(5)

(4)

(3)

l

C

H

e

F

3

H

C

2

O

S

2

H

N

4

O

S

2

)

3

H

C

(

H

O

a

N

S

2

a

+ N

H

O

a

N

H

O

5

H

2

C

2

S

2

a

N

3

H

C

2

O

S

2

O

N

2

O

2

H

H

O

O

C

3

H

C

3

H

C

S

2

O

N

H

S

2

O

N

2

O

N

S

S

2

O

N

l

C

2

O

N

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