AeA?AEAAIEE OI?AA?NEOAO “EUeA?ANUeEA IIE?OAOI?EA”

Aoa??e

ci?yia aanee?aia

OAeE 547.5

NEIOAC OA AEANOEAINO? AAI?IAEUeIEO

AeEOEI?IIIO?AeIEO 1,2- ? 1,4-IAOOIO?III?A

02.00.03 — I?AAI?*IA O?I?ss

AAOI?AOA?AO

AeENA?OAOe?? IA CAeIAOOOss IAOEIAIAI

NOOIAIss EAIAeEAeAOA O?I?*IEO IAOE

EUeA?A — 1999

Aeena?oaoe??th ? ?oeiien.

?iaioa aeeiiaia o Aea?aeaaiiio oi?aa?neoao? “Euea?anueea iie?oaoi?ea”

I?i?noa?noaa ina?oe Oe?a?ie

Iaoeiaee ea??aiee: Aeieoi? o?i?/ieo iaoe, i?ioani?

Iia?eia Aieiaeeie? Iaaeiae/

Aea?aeaaiee oi?aa?neoao “Euea?anueea iie?oaoi?ea”,

caa?aeoaa/ eaoaae?e OANIA

Io?oe?ei? iiiiaioe: Aeieoi? o?i?/ieo iaoe, i?ioani?

Oaaeea Ieanue Iaaeiae/,

?inoeooo o?ceei-i?aai?/ii? o?i?? oa aoaeao?i??

?i. E.I. Eeoaeiaiea IAI Oe?a?ie,

caa?aeoaa/ a?aeae?eo

Eaiaeeaeao o?i?/ieo iaoe, aeioeaio

E?oeiaaoeue Ieaen?e Einoyioeiiae/,

Aea?aeaaiee oi?aa?neoao “Euea?anueea iie?oaoi?ea”,

aeioeaio

I?ia?aeia onoaiiaa: ?inoeooo i?aai?/ii? o?i?? IAI Oe?a?ie, a?aeae?e
iaoai?ci?a

i?aai?/ieo ?aaeoe?e, i. Ee?a

Caoeno a?aeaoaeaoueny: “ 1 ” aa?aciy 1999 ?. i 15 aiae. ia
can?aeaii? niaoe?ae?ciaaii? a/aii? ?aaee Ae 35.052.01 o
Aea?aeaaiiio oi?aa?neoao? “Euea?anueea iie?oaoi?ea”: 290646 Euea?a — 13,
ie. Na. TH?a, 3/4 aoae. 240

C aeena?oaoe??th iiaeia iiciaeiieoenue o a?ae?ioaoe? , Aea?aeaaiiai
oi?aa?neoaoo “Euea?anueea iie?oaoi?ea” (aoe. I?ioani?nueea, 1)

Aaoi?aoa?ao ?ic?neaiee “ 30 ” n?/iy 1999 ?.

A/aiee nae?aoa? niaoe?ae?ciaaii? a/aii? ?aaee

eaiaeeaeao o?i?/ieo iaoe, aeioeaio Nei?ioiaea A.E.

CAAAEUeIA OA?AEOA?ENOEEA ?IAIOE

AEOOAEUeI?NOUe ?IAIOE. Ia aeeaey/enue ia a?eueo i?ae noi??/ia aea/aiiy
o?i?? o?iii?a, niieoee oeueiai eeano i?eaa?oathoue aei naaa oaaao ? a
oaia??oi?e /an. Aeine?aeaeaiiy a iaeano? o?ii?aeieo niieoe c?iaeee
nooo?aee aianie o ?icaeoie oai?aoe/ieo canaae i?aai?/ii? o?i??, a
oaeiae aeaee iiaeeea?noue aeyaeoe aaaaoi ?a/iaei, ye? i?iyaeythoue
??ciiiai?oio a?ieia?/io aeoeai?noue (a?ioeeaeio, aioea?ioe/io,
aioeieneaeaioio oa ?io?).

Ne?ae cacia/eoe, ui niieoee c aai?iaeueiei aeeaaeiaai?aeiei o?aaiaioii
aeeeeeathoue oaeiae caoe?eaaeaiiy, ai a?aeiii, ui aaaaeaiiy aoiia oei?o
a o?ii?aeia yae?i ni?ey? aeyaeaiith ianoeoeeaeieo oa ??no?aaoethth/eo
aeanoeainoae, ui, aacnoii?aii, ia? i?aeoe/io ei?enoue c iaoith
canoinoaaiiy a ia?iaeiiio ainiiaea?noa?.

O ca’yceo c iniaeeaith oe?ii?noth o?iii?a, c iaeiiai aieo, ?
iie?oei?iaaieo no?oeoo? c ?ioiai, c’ynoaaiiy aeaoaeae neioaco
aai.-aeeoei?eae?a iaooio?iii?a oa aea/aiiy ?o o?i?/ieo aeanoeainoae
caeaoia i?eaanoe aei oe?eaaeo aeniiae?a, ye? aeiiiaieee a nenoaio
iiaeyae?a i?i ?aaeoe?eio caeaoi?noue aai.-aeeoei?eaeieo no?oeoo? ?
aeaee a ciiao io?eiaoe i?aeoe/ii ei?eni? niieoee.

?iaioa aeeiiaia o a?aeiia?aeiino? c aea?aeaaieie
iaoeiai-oaoi?/ieie i?ia?aiaie 7.03.01. «Iia? ?a/iaeie oa iaoa??aee
iaeioiiaaeiiai o?i?/iiai ae?iaieoeoaa», 03.06.»Iia? aeieia?/ii
aacia/i? e?eoaaeuei? caniae», ui ? i?aeoaa?aeaeaiiyi aeooaeueiino?
oa ia?niaeoeaiino? aeaieo aeine?aeaeaiue.

IAOA ?IAIOE. Neioac, aoaeiaa oa aeanoeaino? aai?iaeueieo aeeoei?eae?a
ai?ii- oa a?ae?iene-1,2- ? 1,4-iaooio?iii?a oa iiaeeea? oeyoe ?o
i?aeoe/iiai canoinoaaiiy.

IAOEIAA IIAECIA. Aia?oa aeine?aeaeaii ?aaeoe?? oei?oaaiiy ai?ii- ?
a?ae?ieneiio?aeieo 1,2- ? 1,4-iaooio?iiio o?ao-aooeea?iioei?eoii ?
io?eiaii aai?iaeuei? aeeoei?eaee iaooio?ii?aeieo nenoai. Aecia/aii
iioeiaeuei? oiiae oa ?ic?iaeai? iaoiaeeee neioaco
aee-o?ao-aooeeoai?ecai?uaieo 1,2- ? 1,4-iaooio?iii?a. Aeine?aeaeaii
o?i?/i? aeanoeaino?
2,3-aeea?ae?i-3,3-aeeoei?i-2-?i?ii(ieni)-1,4-iaooio?iiio a ?aaeoe?yo c
ioeeaio?eueieie ?aaaaioaie (NI-eeneioaie, ai?iaie, eoaaie).
Cai?iiiiiaaii iaoai?cie ia?aa?ao ?aaeoe?e, ye? i?aeoaa?aeaeothoueny
e?iaoe/ieie aeine?aeaeaiiyie. Eaaioiai-o?i?/ieie ?ic?aooieaie
?ioa?i?aoiaaii aca?iiae?th aai.-aeeaaeiaai?ae?a c NI-eeneioaie.

I?AEOE*IA Oe?II?NOUe. ?ic?iaeaii c?o/i? i?aia?aoeai? iaoiaeeee
iaea?aeaiiy ?ai?oa ia iienaieo aaeiaaiiiio?aeieo 1,2- ?
1,4-iaooio?iii?a, a oiio /ene? oaeeo, ui i?noyoue aai?iaeueiee
aeeoei?eaeiee o?aaiaio. A ?acoeueoao? nea?iaaiiai neioaco iiaeo niieoe
c aai?iaeueiei aeeoei?ieaeiei o?aaiaioii, ciaeaeai? ?a/iaeie, ye?
i?iyaeythoue aenieo i?ioeooaa?eoeueicio ? ooia?aaeoa?eoeeaeio
aeoeaiino?. Aeaye? ai?iioei?iiio?aei? 1,4-iaooio?iiio aeei?enoai? ye
iai?ai?iaeoeoe i?e iaea?aeaii? iiaeo aee?i?ic/eiieo aa?aiee?a.

INIAENOEE AIANIE AeENA?OAIOA iieyaa? a i?iaaaeaii? aenia?eiaioaeueieo
aeine?aeaeaiue, ia?iaoe? io?eiaieo ?acoeueoao?a, oi?ioethaaii?
iniiaieo iieiaeaiue ? aeniiae?a aeena?oaoe?eii? ?iaioe.

AI?IAAOe?ss ?IAIOE. Iniiai? ?acoeueoaoe ?iaioe aeiiia?aeaeenue ia
iaoeia?e eiioa?aioe?? «I?iaeaie i?aai?/iiai neioaco» (Euea?a,1994), ia
XVII Oe?a?inuee?e eiioa?aioe?? c i?aai?/ii? o?i?? (Oa?e?a,1995), ia
oino?e iaoeia?e eiioa?aioe?? «Euea?anuee? o?i?/i? /eoaiiy — 97» (Euea?a,
1997) oa iaoeiai-oaoi?/ieo eiioa?aioe?yo Aea?aeaaiiai
oi?aa?neoaoo «Euea?anueea iie?oaoi?ea» a 1994-1998 ?ieao.

IOAE?EAOe??: Ca oaiith aeena?oaoe?eii? ?iaioe iioae?eiaaii 5 noaoae ? 3
oace aeiiia?aeae.

IA’?I ?IAIOE. Aeena?oaoe?eia ?iaioa aeeeaaeaia ia 153 noi??ieao
iaoeiiieniiai oaenoo, neeaaea?oueny c? anooio, i’yoe ?icae?e?a,
aeniiae?a, nieneo aeei?enoaieo aeaea?ae c? 135 iaeiaioaaiue,
aeiaeaoe?a, i?noeoue 8 oaaeeoeue, 28 ?enoie?a, 2 noaie.

INIIAIEE CI?NO ?IAIOE

Neioac aai?iaeueieo aeeoei?eae?a

ai?ii- oa a?ae?ieneiio?aeieo 1,2- ? 1,4-iaooio?iii?a?a

Ia’?eoaie aeine?aeaeaiiy aoee aea?ai? eaaeiaeinooii? ai?ii-,
a?ae?ieneiio?aei? 1,2- oa 1,4-iaooio?iiie. C e?oa?aoo?ieo aeaea?ae
a?aeiii, ui o?ao-aooeea?iioei?io ? oeiiaei oei?ioth/ei aaaioii
??ciiiai?oieo acioiai?nieo niieoe, oiio oe?eaai aoei canoinoaaoe eiai
aeey aaeiaaioaaiiy a?ae?ieneiio?aeieo 1,4-iaooio?iiio.

Aoeaoeeai?iiiio?aeia 1,4-iaooio?iiio (1), ii??aithth/e c
2-ai?ii-1,4-iaooio?iiiii ?aaao? c o?ao-aooeea?iioei?ioii iia?euei?oa
? eeoa i?e iaa??aaii?. A ?acoeueoao? ooai?th?oueny ia
2-N-oei?aoeaoeeai?ii-1,4-iaooio?iii, a
2-aoeaoeeai?ii-3-oei?i-1,4-iaooio?iii (2) oi/a ?ai?oa aoei iienaii, ui
?aaeoe?y oei?oaaiiy 2-aoeaoeeai?ii-3-oei?i-1,4-iaooio?iiio (2) eaea
c? ci?iith eii?aeeiaoe?? oei?o a iaioaae? >N-C=C-C=O ?c io?eiaiiyi
aeeeth/ii 2-N-oei?aoeaoeeai?ii-3-oei?i-1,4-iaooio?iiio (3).

O?ceei-o?i?/i? eiinoaioe (OOO, O.ie., ?* niaeo?) iaea?aeaii? ?a/iaeie
(2) ?aeaioe/i? c aeaieie aeey
2-aoeaoeeai?ii-3-oei?i-1,4-iaooio?iiio, aeiaooiai cono??/iei neioacii —
aoeeethaaiiyi 2-ai?ii-3-oei?i-1,4-iaooio?iiio (4) .

I?ioean oei?oaaiiy 2-aoeaoeeai?ii-1,4-iaooio?iiio (1) iiaea
cae?enithaaoeny ca e?eueeiia ia?o?ooaie. Aiaeia?/i? noaie iiaeooue aooe
cai?iiiiiaai? ? aeey ?ioeo 2-iio?aeieo-1,4-iaooio?iiio.

Ia?o?oo 1. Ooai?th?oueny iaeinoaa?eueiee N-oei?ai?i oeio (1a),
yeee ?ciia?eco?oueny a 2,3-aeea?ae?iniieoeo (2a).

Ia?o?oo 2. ?aaeoe?y iiaea cae?enithaaoeny /a?ac i?iaeoeo i?e?aeiaiiy
(1a) o?ao-aooeea?iioei?eoo ii iiaea?eiiio -N=N- ca’yceo o?iiio (1) c
ianooiiei ae?i?ioaaiiyi o?ao-aooeeiaiai nie?oo e ooai?aiiyi
2,3-aeea?ae?ino?oeoo?e (2a) aai c a?aeuaieaiiyi i?ioiia a?ae
aoaeaoeaaiai aoiia ? i?yiei ooai?aiiyi niieoee (2).

Ia?o?oo 3. ?aae?caoe?y i?ioeano iiaeeeaa /a?ac iaeinoaa?eueiee
eiiieaen (1a) c eiai iiaeaeueoei ia?aoai?aiiyi a ?ioa?iaae?ao (1a)
aai, ui iaea?eueo ?iia??ii, c neio?iiiei a?aeuaieaiiyi i?ioiio a?ae
aoiia acioo e ae?i?ioaaiiyi o?ao-aooien?ai?iio c ooai?aiiyi
2,3-aeea?ae?io?iiio (2a).

Ia?o?oo 4 ? 4a. E?iaoe/ii aea?aeiei oeaio?ii eii?aeeiaoe??
aeaeo?io?eueiiai oei?o, aiaeia?/ii aei aoeaoai?ae?a, ? aoii eenith.
Oiae? ?aaeoe?y iiaea ?aae?ciaoaaoenue /a?ac ?ioa?iaae?aoe (1a)
aai (1ae), ye? aeai?ioiiothoueny c ianooiiei I-N /e I-N oei?iei cnoaii
? ia?aoai?ththoueny a 2,3-aeea?ae?iniieoeo (2a).

I?ioean oei?oaaiiy
2-(4-a?ae?iene-3,5-aee-o?ao-aooeeoai?e)-1,4-iaooio?iiio (5) ? a?eueo
o?eaaeei i?ae aeey 2-a?ae?iene-1,4-iaooio?iiio, ?iia??ii /a?ac
i?inoi?ia? oo?oaeiaiiy oa aeayeo noaa?euei?noue i?ii?aeieo o?iieaaeo
nenoai. Iiynieoe ooai?aiiy
2-(4-a?ae?iene-3,5-aee-o?ao-aooeeoai?e)-3-oei?i-1,4-iaooio?iiio (6)
iiaeia aeoiaey/e c i?eioeeio caa?aaeaiiy i?a?oaeueii? neiao???. A
iaoiio aeiaaeeo ia? i?noea ia?aeiiee [1,3]-cnoa aoiia oei?o ia
N3-aeaeo?io?eueiee oeaio? c ianooiiith [1,7]-aioa?iiiaa?oiaaith,
oa?i?/ii aeicaieaiith, neaiao?iiiith i?a?aoe??th aoiia aiaeith. I?e
oeueiio noa?e/ia neiao?e/ia i?a?oaeue aiaeith ia?ae?eaa?oueny c
p-aeieyie c i?ioeeaaeiiai aieo  p-cenoaie ?ioa?iaae?aoo (6a) ?
oa?aeoa?eco?oueny a?nnth neiao??? ae?oaiai ii?yaeeo.

Aoaeiao niieoee (6) aoei i?aeoaa?aeaeaii o?ceei-o?i?/ieie iaoiaeaie
aiae?co oa cono??/iei neioacii — aca?iiae??th
2,3-aeeoei?i-1,4-iaooio?iiio c 2,6-aee-o?ao-aooeeoaiieii.

Neioace ia iniia? aee-o?ao-aooeeoai?ecai?uaieo iaooio?iii?a oe?eaa? c
oi/ee ci?o aea/aiiy iiaaae?iee niieoe c i?inoi?iai-ae?aiiaaiei
cai?nieeii. C i?eeeaaeiiai aieo — ?a/iaeie oaeiai oeio oe?iei a?aeii? ye
?aaoeyoi?e ?inoo ?ineei, na?oeinoaa?e?caoi?e, ethi?iioi?e oa
??ciiiai?oi? e?ea?nuee? caniae.

Aa?o/e aei oaaae oeae oaeo, cae?eniaii aca?iiae?th
2-(4-a?ae?iene-3,5-aee-o?ao-aooeeoai?e)-3-oei?i-1,4-iaooio?iiio (6) c
1,2,3-aaicio?eacieii. ?aaeoe?th i?iaiaeeee a nie?oiai-eoaeiiio
na?aaeiaeu? i?e iaa??aaii? ?aaeoe?eii? iane aei 80 0N.

?icaeyaeath/e aoaeiao iieaeoee
2-(4-a?ae?iene-3,5-aee-o?ao-aooeeoai?e)-3-(1,2,3-aaicio?eacie?e)-1,4-iao
oio?iiio (7), aa/eii iiaeeea?noue ?nioaaiiy i?ioio?iiieo ia?aoai?aiue,
ye? iiyniththoueny, aia?aaoe/iith aea?aei?noth ooai?aiiy
eaac?a?iiaoe/iiai oeeeeo, aiane?aeie c’?aeiaiiy aioo??iieaeoey?iei
aiaeiaaei ca’yceii aeaio eii’thaiaaieo /anoei iieaeoee
(aaicio?eacieueiiai o?aaiaioo ? o?iiiiaiai e?eueoey), aiaeia?/ii ye a
iienaiiio aeiaaeeo c aaiacieii I. A ?* niaeo?? niieoee (7), caienaiiio
a ?ic/ei? iaoeeaioei?eaeo iayaia aocueea nioaa iiaeeiaiiy i?e 3646
ni -1, oa?aeoa?ia aeey aaeaioieo eieeaaiue a?ae?ieneeueii? a?oie
oai?eueiiai e?eueoey. I?e caienoaaii? ?* niaeo?o ?a/iaeie (7) a AeIOA
nioaa iiaeeiaiiy aaeaioieo eieeaaiue a?ae?ienea?oie niinoa??aa?oueny
aaea i?e 3548 ni-1, oiaoi a iaeano? aioo??iieaeoey?iiai aiaeiaaiai
ca’yceo (7a). Oaea ea?oeia ?icoaooaaiiy nioa iiaeeiaiiy II-a?oi a
?* niaeo?ao i?iaeoeoo (7), a oaeiae iayai?noue ?ciaanoe/ii? oi/ee a
OO-niaeo?ao, ca?a?no?iaaieo a ??cieo ?ic/eiieeao na?ae/eoue i?i
iiaeeea?noue i?ioio?iiieo ia?aoai?aiue.

?ai?oa aoee iienai? niieoee, ye? iathoue ea?aii?eueio ? ai?iia?oie,
?icae?eai? iinoeeii -N=N-N< ? ye? iiaeooue caciaaaoe i?ioio?ii??. C iaoith ?icoe?aiiy niaeo?o iiae?aieo nenoai i?iaiaeeeenue ?aaeoe?? 2-aoeaoeeai?ii- (2) oa 2-a?ae?iene-3-oei?i-1,4-iaooio?iiio (8) c o?eaoeeai?iii a aaicie?, a ?acoeueoao? /iai ooai?ththoueny /aoaa?oeii? aiii?ei? nie?. A ?* niaeo?? i?iaeoeoo aca?iiae?? o?iiio (2) , a?aenooiy nioaa iiaeeiaiiy, oa?aeoa?ia aeey NI-a?oie, a nioaa iiaeeiaiiy ea?aii?eueieo a?oi iaeaea ia ci?uaia (  SYMBOL 110 \f "Symbol" \s 12 n  N=I 1675 ci -1), ui aiai?eoue i?i /?oeo eii?aeeiaoe?th ia ?aaeoe?eieo oeaio?ao (nei??oa anueiai ia N3 ). Ie??i oiai, iayai?noue nioa iiaeeiaiiy a ?ioa?aae? 2800-2380 ni -1, i?eoaiaii?e aeey aiii?eieo a?oi na?ae/eoue i?i ia?aiin i?ioiio c o?ii?aeiiai o?aaiaioo ia acioio iniiao. 2-A?ae?iene-3-oei?i-1,4-iaooio?iii (8) aca?iiae?? c o?eaoeeai?iii, ooai?thth/e n?eue, caaa?aeaio a /a?aiiee eie??, oi/a aeo?aeiee iaooio?iii (8) - aeiaoiai eieuei?o, ui na?ae/eoue i?i iayai?noue a iiaiooai?ai?e niieooe? o?iiioi?ii? nenoaie -I-N=N-N=I. Iiaeeeai, ui a aeaiiio aeiaaeeo ooai?th?oueny n?eue c eii?aeeiaoe??th o?eaoeeaiii?th ia aoii? eenith, ui iiaeia i?aeoaa?aeeoe iineeath/enue ia a?aenooi?noue a ?* niaeo?? nioae iiaeeiaiiy, oa?aeoa?ii? aeey aaeaioieo eieeaaiue a?ae?ieneeueieo a?oi, a a ?ioa?aae? 2800-2380 ni-1 - iayai?noue nioa iiaeeiaiiy, aeanoeaeo aeey aiii?eieo a?oi. Oaeei /eiii, aeey o?eaoeeaiii?eieo nieae aoeaoeeai?iioei?iiio?aeiiai (2) iaea?eueo a??ia?aeiith aoaeiaith aoaea no?oeoo?a (9a), a aeey a?ae?ieneiio?aeiiai (8) - no?oeoo?a (9a). C iaoith io?eiaiiy iaooio?ii?aeieo niieoe c aai?iaeueiei aeeoei?iai?niei o?aaiaioii, a oaeiae c iaoith aecia/aiiy eii?aeeiaoe?? aoiia oei?o i?e oei?oaaii? 2-ai?ii- ? 2-a?ae?iene-3-oei?i-1,4-iaooio?iii?a, i?iaiaeeany aenia?eiaio a oeo aea oiiaao, ui ? oei?oaaiiy 2-cai?uaieo iaooio?iii?a ?c canoinoaaiiyi o?ao-aooeea?iioei?eoo ye aaeiaaioth/iai aaaioo. Aia?oa anoaiiaeaii, ui ?aaeoe?y 2-a?ae?iene-3-oei?i-1,4-iaooio?iiio (8) c o?ao-aooeea?iioei?eoii i?eaiaeeoue aei ooai?aiiy 2,3-aeea?ae?i-3,3-aeeoei?i-2-ieni-1,4-iaooio?iiio (10), a ia aei 1-a?ae?iene-2,2-aeeoei?i-3-ieni?iaeai-1-ea?aiiiai? eeneioe, ye aoei iieacaii i?e oei?oaaii? a eoaeiiio na?aaeiaeu?. Ooai?aiiy 2,3-aeea?ae?i-3,3-aeeoei?i-2-ieni-1,4-iaooio?iiio (10) i?aeoaa?aeaeo?oueny iayai?noth a ?* niaeo?? nioae iiaeeiaiiy ea?aii?eueieo a?oi a iaeano? 1720 ni -1, 1725 ni -1 ? a?aenooi?noth iiaeeiaiiy, oa?aeoa?iiai aeey aaeaioieo eieeaaiue a?ae?ieneeueii? a?oie. Cai?ia a?ae?ienea?oie a 2-a?ae?iene-3-oei?i-1,4-iaooio?iiiia?e nenoai? ia aenieiaeaeo?iiiaeiii?io 2,6-aee-o?ao-aooeeoaiieueio a?oio iiaeiii ae i?ecaanoe aei ca?eueoaiiy ?? ?aaeoe?eii? caeaoiino? noiniaii aei o?ao-aooeea?iioei?eoo. A oie aea /an, anoaiiaeaii, ui 2-(4-a?ae?iene-3,5-aee-o?ao-aooeeoai?e)-3-oei?i-1,4-iaooio?iii (6) ?aaao? c o?ao-aooeea?iioei?eoii cia/ii iia?euei?oa ii??aiyii c 2-a?ae?ieneiio?aeiei (8) (2 aiae. ? 3,5 aiae., a?aeiia?aeii). Ia?iaea 2-(4-a?ae?iene-3,5-aee-o?aoaooeeoai?e)-3-oei?i-1,4-iaooio?iiio (6) o?ao-aooeea?iioei?eoii aaaea aeeeth/ii aei 2,3-aeea?ae?i-3,3-aeeoei?i-2-(4-ieni-3,5-aee-o?ao-aooee-2,5-oeeeeiaaenaa e??i?e?aeai)-1,4-iaooio?iiio (11). Ci?uaiiy nioae iiaeeiaiiy ea?aii?eueii? a?oie a ?* niaeo?? aeeaaeiaai?aeo (11) o aeniei/anoioio iaeanoue ( SYMBOL 110 \f "Symbol" \s 12 n  N=I 1718-1710 ni -1), o ii??aiyii? c aeo?aeiei o?iiiii (6) ( SYMBOL 110 \f "Symbol" \s 12 n  N=I 1648-1640 ni -1), na?ae/eoue i?i a?aenooi?noue a iieaeoe? (11) o?ii?aeii? nenoaie ca’yce?a. A ?ic/ei? aeaeoa??eoei?ioi?io i?e aioo??oiueiio noaiaea?o? OIN niaeo? II? iieno?oueny aeaiia neiaeaoaie a?n?iiaaeoeyoe i?ioii?a oanoe iaoeeueieo a?oi aeaio o?ao-aooeeueieo o?aaiaio?a i?e 1,187 i.ae. ? 1,264 i.ae., aeaiia aeoaeaoaie aeaio i?ioii?a oeeeeiaaenaae??i?e?aeaiiaiai cai?nieea i?e 6,49 i.ae. ? 6,61 i.ae., a oaeiae ioeueoeieaoii /ioe?ueio a?iiaoe/ieo i?ioii?a iaooae?iiaiai e?eueoey i?e 7,82 i.ae. ? 8,198 i.ae. Oaea aiiiaeueii iecueea ?aaeoe?eia caeaoi?noue a ?aaeoe?yo c o?ao-aooeea?iioei?eoii niieoee (6), ii??aithth/e c 2-a?ae?iene-3-oei?i-1,4-iaooio?iiiii (8), ?iia??ii, iia’ycaia c? noa?e/ieie ia?aoeiaeaie, a oaeiae i?aeaeuaiith noaa?euei?noth a?iioaoe/iiai ea?aeao?iio (11a) ca ?aooiie aeaeieae?caoe?? ca?yaeo ia aee-o?ao-aooeeoaiieueiiio o?aaiaio?. Ie??i oiai, ia aeeeth/aii ooai?aiiy a?aeiinii noaa?eueiiai aaeiaaio?iieueiiai iio?aeiiai c ianooiiei eiai ia?aoai?aiiyi a a?eueo noaa?eueiee 2,3-aeea?ae?i-3,3-aeeoei?i-2-(4-ieni-3,5-aee-o?ao-aooee-2,5-oeeeeiaaenaa e??i?e?aeai)-1,4-iaooio?iii (11). Aiaeia?/ii a?aeaoaa?oueny aca?iiae?y 4-(4-a?ae?iene-3,5-aee-o?aoaooeeoaiie)-3-oei?i-1,2-iaooio?iiia (12) c o?ao-aooeea?iioei?ieoii, aea cia/ii iia?euei?oa, i?ae o aeiaaeeo iio?aeiiai o?iiia (6). Ciaioaiiy ?aaeoe?eii? caeaoiino? niieoee (12) iiynith?oueny iiaeeeai oei, ui ea?aeao?ii (12 a) a aeaiiio aeiaaeeo ? a?eueo noaa?eueiee ca ?aooiie aeaeieae?caoe?? iiceoeaiiai ca?yaeo ia aee-o?ao-aooeeoaiieueiiio ? oai?eueiiio o?aaiaioao o?iiio, a oaeiae noa?e/ieie oo?oaeiaiiyie aoaee  ?aaeoe?eiiai oeaio?o N3 iiceoeaii ca?yaeaeaiei eao?iiii oei?o aai, iiaeeeai, a?eueoith noaa?euei?noth aaeiaaio?iieueii? no?oeoo?e. Aoaeiaa 3,4-aeea?ae?i-3,3-aeeoei?i-4-(4-ieni-3,5-aeeo?ao-aooee-2,5-oeeeeiaaenaae ??i?e?aeai)-1,2-iaooio?iiia (13) i?aeoaa?aeaeo?oueny aeaieie ?* niaeo?a, a yeiio niinoa??aa?oueny nioaa iiaeeiaiiy ea?aii?eueieo a?oi o a?eueo aeniei/anoioi?e iaeano? ( SYMBOL 110 \f "Symbol" \s 12 n  N=I 1720 ni -1), a ii??aiyii? c aeo?aeiei iiiioei?eaeii (12) ( SYMBOL 110 \f "Symbol" \s 12 n  C=I 1675 ni -1), ui na?ae/eoue i?i ao?aoo iaooio?iiiiaei e?eueoeai o?ii?aeii? nenoaie ca’ye?a. A ?ic/ei? aeaeoa??eoei?iioi?io i?e aioo??oiueiio noaiaea?o? OIN niaeo? II? i?noeoue neaiaee a?n?iiaaeoeyoe i?ioii?a oanoe iaoeeueieo a?oi aeaio o?ao-aooeeueieo o?aaiaio?a o aeaeyae? aeaio neiaeao?a i?e 1,191 i.ae. ? 1,279 i.ae., aeaa aeoaeaoe aeaio i?ioii?a oeeeeiaaenaae??i?e?aeaiiaiai cai?nieea i?e 6,47 i.ae. ? 6,62 i.ae., ? ioeueoeieao i?ioii?a iaooio?iiiiaiai e?eueoey i?e 7,76 i.ae. ? 8,24 i.ae. I?e cai?i? a?ae?ienea?oie ia ai?iia?oio o ae?oaiio iieiaeaii? 3-oei?i-1,4-iaooio?iiiiaiai o?aaiaioo, niinoa??aa?oueny i?aeaeuaiiy ?aaeoe?eii? caeaoiino? o?iiio. Oae, 2-ai?ii-3-oei?i-1,4-iaooio?iii (4) oei?o?oueny o?ao-aooeea?iioei?ieoii i?ioyaii 0,3 aiae aei 3,3-aeeoei?ino?oeoo?e (15). Oea, eiia??ii, iiaycaii c? ciaioaiiyi noaa?eueiino? ea?aeao?iio niieoee (4) ? aenieith oaeaee?noth eiai aeai?ioiioaaiiy. Aeinoia??i?noue cai?iiiiiaaii? no?oeoo?e (15) i?aeoaa?aeaeo?oueny niaeo?ii ssE? 35Nl, a yeiio iayai? neaiaee aoiia oei?o ca’yceo N-Nl i?e 38,069 IAoe oa 39,720 IAoe aeey niieoee (14) ? 39,058 IAoe, 39,959 IAoe aeey niieoee (15). Iiaeaeueoa oei?oaaiiy ai?iiiaooio?iiio (4) i?ecaiaeeoue aei iiyae e??i neaiae?a aoiia oei?o ca’yceo N-Nl, neaiaeo aoii?a oei?o ca’yceo >N-Cl a iaeano? 48-49 IAoe a niaeo?ao ssE?  35 Nl.

Anoaiiaeaii ui, N-a?eethaaiiy 2-ai?iicai?uaieo 1,4-iaooio?iiio ia
aieeaa? ia naeaeoeai?noue i?ioeano. Ci?uaiiy a?eueii? aeaeo?iiii? ia?e
aoiia acioo ia a?eeueiee o?aaiaio iaei ae i?eaanoe aei i?ii?aeiiai
i?iaeoeoo c ca’yceii >N-Cl, aea aeae?eeoe N-oei?ai?i /e cao?enoaaoe c
aeiiiiiaith OOO /e ?* niaeo?ineii?? ia aaeaeiny. Ioaea, ?aaeoe?y eaea
aeeeth/ii c ooai?aiiyi
2-N-a?eeai?ii-2,3-aeea?ae?i-3,3-aeeoei?i-1,4-iaooio?iii?a (20-23).

Aoaeiaa aai.-aeeoei?eae?a (20-23) i?aeoaa?aeaeaia o?ceei-o?i?/ieie
iaoiaeaie aiae?co. Aeniei/anoioia nioaa iiaeeiaiiy i?e 1725-1722 ni
-1 a ?* niaeo?ao i?iaeoeo?a oei?oaaiiy (20-23) na?ae/eoue i?i
a?aenooi?noue ni?yaeaiiy i?ae a?oiaie N4 =I ? >C=N-. A niaeo?ao ssE?
 35 Cl ia? i?noea ??cea ca?eueoaiiy /anoio aoii?a oei?o. Neaiaee
i?iyaeythoueny o aeaeyae? aeoaeao?a ? eaa?oao?a a iaeano? 38-49 IAoe,
oa?aeoa?i?e aeey aai.-aeeoei?eaeieo o?aaiaio?a.

I?iaaaeai? e?iaoe/i? aeine?aeaeaiiy ia i?eeeaae? oei?oaaiiy
2-oai?eai?ii-3-oei?i-1,4-iaooio?iiio (16) o?ao-aooeea?iioei?eoii o
aaicie? iieacaee, ui a oiiaao iaaeeeoeo oei?oth/iai aaaioa ?aaeoe?y
i?io?ea? ca ia?oei ii?yaeeii ii aeo?aei?e ?a/iaei?; anoaiiaeai?
iioeiaeuei? oiiae iaea?aeaiiy
2,3-aeea?ae?i-3,3-aeeoei?i-2-oai?e?i?ii-1,4-iaooio?iiio (20) (i?e
N0=0,005 iieue/ e, t=20°C, 0,3 aiae.)

Aca?iiae?y aai.-aeeoei?i-1,4-iaooio?iii?a

c ioeeaio?eueieie ?aaaaioaie

Aacnoii?aii, ? aeioe?eueiei aecia/aiiy ?aaeoe?eii? caeaoiino?
aai?iaeueieo aeeaaeiaai?ae?a iaooio?iiiiaeo nenoai, ye? aeioaia?
caeeoaeenue iica oaaaith, ui aeicaieeoue ?icoe?eoe oai?aoe/i? oyaeaiiy
a aeai?e iaeano? ? ciaeoe iia? i?aeoe/ii ei?eni? a?ieia?/ii aeoeai?
niieoee. Uia caiiaieoe oeth i?iaaeeio aea/aeanue ?aaeoe?eia
caeaoi?noue 2,3-aeea?ae?i-3,3-aeeoei?i-1,4-iaooio?iii?a a ?aaeoe?yo c
aeayeeie ioeeaio?eueieie ?aaaaioaie, yeeie ? a?iiaoe/i? ai?ie,
NI-eeneioe, a?ae?aceie oa eoae.

C ?acoeueoao?a aiae?co i?iaeoeo?a aca?iiae??
2,3-aeea?ae?i-3,3-aeeoei?i-1,4-iaooio?iiio (10, 20-23) c a?iiaoe/ieie
ai?iaie (ai?e?iii ? oieo?aeeiii) aeaeii, ui iaeaeaa aoiie oei?o i?enooi?
a yae?? ooai?aii? niieoee (24-28). I/aaeaeii, a?aeaoaa?oueny
i?e?aeiaiiy ioeeaio?eueiiai ?aaaaioa aei N=N /e N=I ca’yceo.

C?icoi?ei, ui ianooiiith noaae??th oaeiai iaoai?cio iaei ae aooe
a?aeuaieaiiy a?aeo?aeii? a?oie. Aea a ?* niaeo?ao io?eiaieo niieoe
i?enooi? aea? /?oe? nioae iiaeeiaiiy, oa?aeoa?i? aeey aaeaioieo
eieeaaiue NI-a?oi a iaeano? 3450-3400 ni-1 aeey iio?aeieo
2,3-aeea?ae?i-3,3-aeeoei?i-2-a?ee?i?ii-1,4-iaooio?iiio (24-26), a
oaeiae a iio?aeieo 2,3-aeea?ae?i-3,3-aeeoei?i-2-ieni-1,4-iaooio?iiio
(27-28) iayaia oe?iea nioaa iiaeeiaiiy a ?ioa?aae? 3600-3400 ni -1, yea
i?eoaiaiia aaeaioiei eieeaaiiyi II-a?oi, a ii?o/ ?icoaoiaaia ?ioaineaia
nioaa iiaeeiaiiy i?e 3350 ni -1, oa?aeoa?ia aeey aaeaioieo eieeaaiue
NI-a?oi. Nioae iiaeeiaiiy ea?aii?eueieo a?oi niinoa??aathoueny a
iaeano? 1750, 1620 ni -1, oa?aeoa?i?e aeey
2,3-aeea?ae?i-3,3-aeeoei?ino?oeoo?. Ca?aene iiaeia ae?eoe aeniiaeo, ui
i?ioean coieiy?oueny ia noaae?? i?e?aeiaiiy ioeeaio?eueiiai caeeoeo.

C iaoith aecia/aiiy iniaeeainoae aca?iiae?? aai.-aeeoei?ieae?a
1,4-iaooio?iiio c a?eueo aei?noeeie ioeeaio?eueieie ?aaaaioaie, i?ae
ai?e?i oa oieo?aeei, aea/aeenue ?o ?aaeoe?? c a?ae?aceiaie.

C ?acoeueoao?a i?iaaaeaii? aca?iiae??
2,3-aeea?ae?i-3,3-aeeoei?i-2-oai?e?i?ii-1,4-iaooio?iiio (20) c
a?ae?aceiaie a i?enooiino? o?eaoeeai?io iiaeia ae?eoe aeniiaeo, ui
?aaeoe?y i?ecaiaeeoue aei ooai?aiiy 1,4-iaooio?ii?aeii? no?oeoo?e. Oae
ye a aeaiiio aeiaaeeo a ?aaeoe?? aa?a o/anoue c iaeiiai aieo, a?ae?acei,
a yeiai aoii aiaeith a?ae?aceiii? a?oie ? aeoeaioi?ii aeaeo?ii?a,
a c ?ioiai aieo — 1,4-iaooio?iiiiaa no?oeoo?a, yea ia? ia eeni?
iaiiae?eaio ia?o aeaeo?ii?a ? aenooia? aeiii?ii, oi ? iiaeeeaei
ooai?aiiy aeiii?ii-aeoeaioi?iiai eiiieaeno.

?iia??ii, a aeaiiio aeiaaeeo a?aeaoaa?oueny naeaeoeaia oei?oaaiiy
aai.-aeeoei?ieaeii (20) a?ae?aceio (i?i oea na?ae/eoue ooai?aiiy
i?iaeoeo?a ?iciaaeo N-oei?ia?ae?acei?a a ?aaeoe?eiiio ?ic/ei?) c
iaeii/aniei a?aeiiaeaiiyi oeeeeiaaenaiiaiai o?aaiaioo aeo?aeiiai
aeeoei?eaeo (20) aei e?ioeaaiai o?ii?aeiiai i?iaeoeoo (16). I?ioean
a?aeaoaa?oueny neio?iiii e i?aeii?yaeeiao?oueny i?eioeeiai caa?aaeaiiy
i?a?oaeueii? neiao???.

Ooai?aiiy 2-oai?eai?ii-3-oei?i-1,4-iaooio?iiio (16)
i?aeoaa?aeaeo?oueny ca?aii eiai o?ceei-o?i?/ieo eiinoaio c eiinoaioaie
aiaeiaa, io?eiaiiai aeueoa?iaoeaiei oeyoii.

Aca?iiae?y 2,3-aeea?ae?i-3,3-aeeoei?i-2-oai?e?i?ii-1,4-iaooio?iiio (20)
c ??cieie NI-eeneioaie a oiiaao ?aaeoe?? I?oaaey a?aeaoaaeanue eaaei oa
?c caaeia?eueieie aeoiaeaie.

Noaey/e c ii??aiyiiy o?ceei-o?i?/ieo eiinoaio
2-oai?eai?ii-3-oei?i-1,4-iaooio?iiio (16), iaea?aeaiiai cono??/iei
neioacii, c eiinoaioaie i?iaeoeo?a ?aaeoe?? iiaeia ae?eoe aeniiaeo, ui
NI-eeneioe a aeaiiio aeiaaeeo aaaeooue naaa ye a?aeiiaethth/? aaaioe,
oi/a ? aeiioneaeanue iiaeeea?noue ioeeaio?eueiiai i?e?aeiaiiy aei N=N
ca’yceo. ?iia??ii, a?aeaoaa?oueny i?io?eaiiy ?aaeoe?? ioeeaio?eueiiai
cai?uaiiy a a?iiaoe/iiio ?yaeo /a?ac i?ii?aeia ooai?aiiy
ai?ii-?aaeeeaeo, oiaoi ca noaiith:

Anoaiiaeaii, ui o aeiaaeeo c
2,3-aeea?ae?i-3,3-aeeoei?i-2-ieni-1,4-iaooio?iiio (10) ? aoeaoiioeoiaei
ao??ii niinoa??aa?oueny ?ioa ea?oeia. I/aaeaeii, ?aaeoe?y
a?aeaoaa?oueny ca iaoai?ciii ioeeaio?eueiiai i?e?aeiaiiy aei iiaea?eiiai
ca’yceo aoaeaoeue-eenaiue.

Ia?aeiiei, ia iao iiaeyae, ? i?e?aeiaiiy c ooai?aiiyi ai?iiiiai
?ioa?iaae?aoo (10a), yea iiaeia ?icaeyaeaoe ye nai???aeiee aeiaaeie
a?iieaeoey?iiai ioeeaio?eueiiai cai?uaiiy. Ioeeaio?eueiee ?aaaaio
aoaeo? aoii aoaeaoeth, ui iana iiceoeaiee ca?yae, a a ?ie? a?aeo?aeii?
a?oie aenooia? a?oia aeaeo?ii?a   SYMBOL 112 \f «Symbol» \s 12 p
-ca’yceo, yea ia?ai?ua?oueny aei eenith, eio?ee iaaeae? iiaea
i?e?aeiaoe i?ioii ? aeaoe i?iaeoeo i?e?aeiaiiy.

Oaeei /eiii, aca?iiae?y iio?aeieo 2-?i?ii- ?
2-ieni-3,3-aai.-aeeoei?i-1,4-iaooio?iii?a c NI-eeneioaie iiaea
a?aeaoaaoeny ca ??cieie iai?yiaie. Aeey iiyniaiiy oaei? a?aei?iiino?
i?iaiaeeeenue eaaioiai-o?i?/i? ?ic?aooiee ia?aa?ao oeeo ?aaeoe?e.
Ca?aeii ?ic?aooie?a iiaeia c?iaeoe aeniiaie, ui ooai?aiiy i?iaeoeoo
a?aeiiaeaiiy o aeiaaeeo c niieoeith (10) ? iaaea?aeiei, ai o i?ioean?
?aaeoe?? niinoa??aa?oueny noaa?e?caoe?y nenoaie (10) caaaeyee
ca?eueoaiith aeaeo?iiii? aonoeie ia aoiiao eenith.

Oe?eaai a?aecia/eoe iacae/i?noue i?io?eaiiy aca?iiae??
2,3-aeea?ae?i-3,3-aeeoei?i-2-oai?e?i?ii-1,4-iaooio?iiio (20) c eoaii a
nie?oiaiio na?aaeiaeu?, yea a?aeaoaa?oueny c? caoaeaiiyi oeeeeo.

I?ioean a?aeaoaa?oueny iinoaae?eii oaeei /eiii, ui nii/aoeo a
eoaeiiio na?aaeiaeu? i?ioiaeeoue aeaea?aieneethaaiiy
1-oai?eai?ii-2,2-aeeoei?i-3-ieni?iaeai-1-ea?aiiiai? eeneioe c ianooiiei
a?aeuaieaiiyi oei?iaiaeith. E?ioeaaee i?iaeoeo (30) iiaea oai?aoe/ii
?nioaaoe o o?ueio oi?iao caaaeyee i?ioio?iii?e i?a?aoe?? i?ioiio a
ieni?iaeaiiaiio e?eueoe?. A ?* niaeo?? niieoee (29) iayaia oe?iea nioaa
iiaeeiaiiy a ?ioa?aae? 3300-3600 ni -1, yea iiaea aooe oa?aeoa?ia aeey
aaeaioieo eieeaaiue ye aeey NI-a?oie, oae ? aeey aeey II-a?oie, a
iaeano? 2928 ni -1, 2856 ni -1 i?enooi? nioae iiaeeiaiiy NI-a?oi, a
ea?aii?eueia a?oia i?aaenoaaeaia aeaui ooe?aiith nioaith a ?ioa?aae?
1703-1682 ni -1 ? oea eieeaaiiy ia iiaea a?aeiia?aeaoe eieeaaiiyi
-N=N-ca’yceo. A?aoiaoth/e iayai?noue ea?aii?eueii? a?oie, iaea?eueo
?iia??ii, i?iaeoeo aca?iiae?? a ?iaeea?aeoaeueiiio oaa?aeiio noai? ?nio?
o oi?i? 1-oai?eai?ii-2-oei?i-3-ieni?iaeai (30a).

Oaeei /eiii, aia?oa a?aee?eoi iiaa ia?aa?oioaaiiy a ?yae? ai?iiiio?aeieo
aai.-aeeoei?eae?a 1,4-iaooio?iiio c? caoaeaiiyi oanoe/eaiiiai
o?ii?aeiiai oeeeeo aei i’yoe/eaiiiai ieni?iaeaiiaiai.

A ?acoeueoao? nea?iaaiiai neioaco ciaeaeai? ?a/iaeie c aenieith
a?ieia?/iith aeoeai?noth c iaoith iiooeo oeyo?a i?aeoe/iiai canoinoaaiiy
neioaciaaieo niieoe.

Iaea?eueo aenieith i?ioeooaa?eoeueiciith aeoeai?noth, yea aeyaeeanue a
iiai?e coieioe? ?inoo oa ?iciiiaeaiiy ooaio i?eiaaeoa??e ooaa?eoeueico
aieiae?thoue
2,3-aeea?ae?i-3,3-aeeoei?i-2-(4-ieni-3,5-aee-o?ao-aooee-2,5-oeeeeiaaenaa
e??i?e?aeai)-1,4-iaooio?iii (11) ?
2,3-aeea?ae?i-3,3-aeeoei?i-4-(4-ieni-3,5-aee-o?ao-aooee-2,5-oeeeeiaaenaa
e??i?e?aeai)-1,2-iaooio?iii (13) oa
2-(4-a?ae?iene-3,5-aee-o?ao-aooeeoai?e)-3-(1,2,3-aaicio?eacie?e)-1,4-iao
oio?iii (7).

Ne?ei?ia neioaciaaieo ?a/iaei ia ooia?aaeoa?eoeeaeio aeoeai?noue
aeicaieea aeyaeoe aeaa aai.-aeeoei?eaeieo ac??oey:
2,3-aeea?ae?i-3,3-aeeoei?i-2-(4-iaoeeoai?e)?i?ii-1,4-iaooio?iii (21) ?
2,3-aeea?ae?i-3,3-aeeoei?i-2-(4-oei?ioai?e)?i?ii1,4-iaooio?iii (22), ye?
i?iyaeythoue aenieo i?eai?/oth/o aeoeai?noue ?inoo Aspergillus niger
(100%) oa aei o?oiooi?ico oiiao?a (90% ? 100%, a?aeiia?aeii) ? oaeei
/eiii iaaeeaeathoueny ca nai?ie iieacieeaie aei aoaeiiiiai i?aia?aoo
OIOAe, a ii a?aeiioaiith aei Fusarium moniliforme oa Venturia inaequolis
ia?aaeuo? eiai.

Neioaciaai? a ?iaio? niieoee aoee aeei?enoai? ye ae?acineeaaeia? i?e
iaea?aeai? iiaeo aee?i?ic/eiieo aa?aiee?a. Cai?iiiiiaai? neioaoe/i?
oeyoe ?o iaea?aeaiiy.

Io?eiai? aa?aieee aoee aei?iaoaai? ia o??i? «Aa?aa» (i.
?aaii-O?aie?anuee), a oaeiae ?ic?iaeaii iia? eaai?aoi?i? ?aaeaiaioe
neioaco aa?aiee?a aee?i?ic/eiiiai /a?aiiiai N oa aee?i?ic/eiiiai
aeiaoiai C.

AENIIAEE

1. A ?acoeueoao? i?iaaaeaieo aeine?aeaeaiue neioaco oa ?aaeoe?eii?
caeaoiino? aai?iaeueieo aeeoei?iiaooio?iii?a c ioeeaio?eueieie
?aaaaioaie anoaiiaeai? caeiiii??iino? ia?aa?ao ?aaeoe?e, ciaeaeai?
iioeiaeuei? oiiae ? aecia/ai? iaoiaee iaea?aeaiiy oeeo niieoe — ana oea
aeaei ciiao cae?enieoe nea?iaaiee neioac ?a/iaei c aaaeaieie ei?enieie
aeanoeainoyie.

2. Anoaiiaeaii, ui oei?oaaiiy 2-ai?ii-, 2-a?ae?iene-1,4-iaooio?iiio
o?ao-aooeea?iioei?eoii i?ecaiaeeoue aei iaea?aeaiiy
N3-aaeiaaiiiio?aeieo, a iiaeaeueoa oei?oaaiiy aaaea aei ooai?aiiy
aai?iaeueieo aeeoei?eae?a; i?e oeueiio cai?iiiiiaaii noaio ia?o?oo?a
?aaeoe?? oei?oaaiiy ? iaea?eueo eiia??iee iaoai?ci io?eiaiiy
aai.-aeeoei?eae?a.

3. ?ic?iaeaii c?o/i? i?aia?aoeai? iaoiaeeee neioaco ??ciiiai?oieo
aaeiaaiiiio?aeieo 1,2- oa 1,4-iaooio?iii?a, a oiio /ene? c
i?inoi?iai-oo?oaeiaieie cai?nieeaie, c aai?iaeueieie aeeoei?eaeieie
oa?oioaaiiyie, aaoa?ioeeee?/ieie o?aaiaioaie oa ?io?. Ia i?aenoaa?
io?eiaieo aenia?eiaioaeueieo aeaieo cai?iiiiiaaii noaie i?ioio?iiieo
i?a?aoe?e o iaooio?ii?aeieo nenoaiao c a?ae?iene- ? ai?iia?oiaie a
noi?aeieo iieiaeaiiyo.

4. E?iaoe/ieie aeine?aeaeaiiyie anoaiiaeaii, ui ooai?aiiy
3,3-aai.-aeeoei?eae?a 1,4-iaooio?iiio ? ?aaeoe??th ia?oiai ii?yaeeo ii
aeo?aeiiio ai?iioei?iiio?aeiiio; anoaiiaeai? iioeiaeuei? oiiae ?o
iaea?aeaiiy (i?e N0=0,005 iieue/ e, t=20°N, 0.3 aiae.).

5. Aeine?aeaeaii aca?iiae?th
2,3-aeea?ae?i-3,3-aeeoei?i-2-?i?ii(ieni)-1,4-iaooio?iiio c
ioeeaio?eueieie ?aaaaioaie: c «aei?noeeie» a?ae?aceiaie ?oeio?oueny
aai.-aeeoei?ieaeiee o?aaiaio ? ooai?th?oueny iaooio?ii?aeia no?oeoo?a; c
«na?aaei?ie» (ai?e?iii oa oieo?aeeiii) i?io?ea? i?e?aeiaiiy inoaii?o
aei N=I aai N=N ca’yceo c? caa?aaeaiiyi aai.-aeeoei?ieaeiiai o?aaiaioo;
o aeiaaeeo «i’yeeo» ea?aai?ii?a NI-eeneio ia?aaaaeii ooai?ththoueny
i?iaeoeoe a?aeiiaeaiiy ai?ii-?aaeeeaeueiiai ia?aa?ao i?ioeano.

6. Eaaioiai-o?i?/ieie ?ic?aooieaie ca i?ia?aiith II?AN ?ioa?i?aoiaaia
aca?iiae?y ?i?ii- ? ieniiio?aeieo 3,3-aeeoei?i-1,4-iaooio?iii?a c
NI-eeneioaie. Iaea?eueo a??ia?aeiei ? ia?aa?a oeeo i?ioean?a ca
ai?ii-?aaeeeaeueiei iaoai?ciii c ooai?aiiyi i?iaeoeo?a a?aeiiaeaiiy
o?ii?aeiiai o?aaiaioo.

7. A?aee?eoi iiaa ia?aa?oioaaiiy a ?yae? ai?iiiio?aeieo
aai.-aeeoei?eae?a 1,4-iaooio?iiio c? caoaeaiiyi oanoe/eaiiiai
o?ii?aeiiai oeeeeo aei i’yoe/eaiiiai ieni?iaeaiiaiai.

8. Na?aae iiaeo neioaciaaieo niieoe ciaeaeai? aoaeoeai? ?a/iaeie, ui
aieiae?thoue i?ioeooaa?eoeueiciith aeoeai?noth; iaea?aeai? niieoee, ui
i?iyaeythoue aenieo i?eai?/oth/o aeoeai?noue ?inoo Asspergillus niger
oa aei o?oiooi?ico oiiao?a, a oaeiae ?a/iaeie, ye? aoee aeei?enoai?
ye ae?acineeaaeia? aeey iaea?aeaiiy iiaeo aee?i?ic/eiieo aa?aiee?a.

Iniiaiee ci?no aeena?oaoe?? aeeeaaeaii a ianooiieo ioae?eaoeeyo:

1. Aoa?ee C.A., Eeai A.C., Eeoaei A.E., Iiaeeia A.I. Iiaua
oei?ii?iecaiaeiua 1,4-iaooioeiiia. // AEo?i.i?a. oeiee. — 1996. — O.32.
— Aui.6. — N.948

2. Aoa?ee C.A., Eeai A.C., Eeoaei A.E., Iiaeeia A.I. Iiaua
oei?ii?iecaiaeiua 1,2-iaooioeiiia. // AEo?i.i?a. oeiee.. — 1996. — O.32.
— Aui.9. — N.1439.

3. Aoa?ee C.A., Eeai A.C., Eeoaei A.E., Iiaeeia A.I. I acaeiiaeaenoaee
2,3-aeeaeae?i-3,3-aeeoei?i-2-oaieeeieii-1,4-iaooioeiiia n NI-eeneioaie.
// AEo?i.i?a. oeiee. — 1998. — O.34. — Aei.1. — N.147.

4. Eeoaei A.E., Aoa??e C.A., Eeai A.C. Ia?aai?ioaaiiy
2-N(R)-ai?ii-3-oei?ii-1,4-iaooio?iiio. // A?niee AeO «Euea?anueea
iie?oaoi?ea». — O?i?y ? oaoiieia?y i?aai?/ieo ?a/iaei. — 1996. — N 298.
— N. 46.

5. Aoa??e C.A., Ei?aeaiaanueea I.A., Oaaei?iaa I.A., Eeoaei A.E.,
Eeai A.C., Iia?eia A.I. I?i iniiai?noue 2-ai?ii-1,4-iaooio?iiio ? eiai
iio?aeieo. // A?niee AeO «Euea?anueea iie?oaoi?ea». — O?i?y ? oaoiieia?y
i?aai?/ieo ?a/iaei — 1997. — N 316. — N 82.

6. Aoa??e C.A., Eeoaei A.E., Oa?an O.I., Eeai A.C., Iia?eia A.I. Neioac
iiaeo ?i?iiaeeoei?iiaooae?iae?ii?a. // Oace aeii. iaoe. eiio.
«I?iaeaie i?aai?/iiai neioaco». — Euea?a — 1994. — N. 122.

7. Aoa??e C.A., Eeoaei A.E., Eeai A.C., Iia?eia A.I. Neioac oa aoaeiaa
2,3-(2I)-2-?i?ii(ieni)-3-aeeaaeiaaiiiaooio?iii?a. // Oace aeii. XVII
Oe?a?inueei? eiioa?aioe?? c i?aai?/ii? o?i??. — Oa?e?a -1995. — N. 76.

8. Aoa??e C.A., Eeai A.C., Eeoaei A.E., Iia?eia A.I. Aca?iiae?y
2,3-aeea?ae?i-3,3-aeeoei?i-2-oai?e?i?ii-1,4-iaooio?iiio c a?ae?aceiaie.
// Oace aeii.oinoi? iaoe.eiio. «Euea?anuee? o?i?/i? /eoaiiy». —
Euea?a-1997. — N. 60.

AIIOAOe??

Aoa??e C.A. Neioac oa aeanoeaino? aai?iaeueieo aeeoei?iiio?aeieo
1,2- ? 1,4-iaooio?iii?a. — ?oeiien.

Aeena?oaoe?y ia caeiaoooy iaoeiaiai nooiaiy eaiaeeaeaoa o?i?/ieo iaoe
ca niaoe?aeuei?noth 02.00.03 — i?aai?/ia o?i?y. — Aea?aeaaiee
oi?aa?neoao «Euea?anueea iie?oaoi?ea», Euea?a, 1998.

Aeena?oaoe?th i?enay/aii ieoaiiyi neioaco oa ?aaeoe?eii? caeaoiino?
aai?iaeueieo aeeoei?iiio?aeieo 1,2- ? 1,4-iaooio?iii?a c ioeeaio?eueieie
?aaaaioaie, ui a?aee?eei iiaeeea?noue aeey iiooeo iiaeo ?a/iaei c
caaeaieie ei?enieie aeanoeainoyie. Oei?oaaiiyi iio?aeieo 1,2- ?
1,4-iaooio?iii?a o?ao-aoo?ea?iioei?eoii iaea?aeaii 3-oei?iiio?aei?, /e?
iiaeaeueo? ?aaeoe?? c o?ao-aooeea?iioei?eoii i?ecaaee aei io?eiaiiy
aai?iaeueieo aeeoei?eae?a. Cai?iiiiiaai? noaie o?i?/ieo ia?aoai?aiue, ia
iniia? yeeo c?iaeaii ni?iao iiyniaiiy o?i?/ieo aeanoeainoae neioaciaaieo
3,3-aeeoei?iiio?aeieo 1,4-iaooio?iii?a i?e aca?iiae?? c ioeeaio?eueieie
?aaaaioaie.

Eeth/ia? neiaa: iaooio?iii, o?ao-aooeea?iioei?eo, aai?iaeuei?
aeeoei?eaee, ioeeaio?euei? ?aaaaioe.

Aoa?ee C.A. Neioac e naienoaa aaieiaeueiuo aeeoei?ii?iecaiaeiuo 1,2- e
1,4-iaooioeiiiia. — ?oeiienue.

Aeenna?oaoeey ia nieneaiea iao/iie noaiaie eaiaeeaeaoa oeie/aneeo iaoe
ii niaoeeaeueiinoe 02.00.03. — i?aaie/aneay oeiey. — Ainoaea?noaaiiue
oieaa?neoao «Eueaianeay iieeoaoieea», Eueaia, 1998.

Aeenna?oaoeey iinayuaia enneaaeiaaieth neioaca e ?aaeoeeiiiie
niiniaiinoe aaieiaeueiuo aeeoei?ii?iecaiaeiuo 1,2- e 1,4-iaooioeiiiia n
ioeeaioeeueiuie ?aaaaioaie, /oi ioe?uei aiciiaeiinoue aeey iienea iiauo
aauanoa n caaeaiiuie iieaciuie naienoaaie.

Iauaeoaie enneaaeiaaaaiey eca?aiu eaaeiaeinooiiua aieii- e
aeae?iene-1,2- e 1,4-iaooioeiiiu. Onoaiiaeaii, /oi eo oei?e?iaaiea
o?ao-aooeeaeiioei?eoii a aaiciea aaaeao e ia?aciaaieth
3-oei?ii?iecaiaeiuo, a i?e aeaeueiaeoai acaeiiaeaenoaee n
o?ao-aooeeaeiioei?eoii ia?acothony aaieiaeueiua aeeoei?eaeu
iaooioeiieaeiuo nenoai. I?e yoii, i?aaeeiaeaiu aiciiaeiua ia?o?oou, ii
eioi?uo iiaeao i?ienoiaeeoue i?ioeann oei?e?iaaiey. No?iaiea
aaieiaeueiuo aeeoei?eaeia iiaeoaa?aeaeaii aeaiiuie yeaiaioiiai aiaeeca,
II?, ssE?, EE niaeo?ineiiee, a oaeaea eeiaoe/aneeie enneaaeiaaieyie
onoaiiaeaii, /oi ia?aciaaiea aaieiaeueiuo aeeoei?eaeia yaeyaony
?aaeoeeae ia?aiai ii?yaeea ii enoiaeiiio aauanoao e ii?aaeaeaiu
iioeiaeueiua oneiaey eo ia?aciaaiey.

?ac?aaioaiu oaeiaiua i?aia?aoeaiua iaoiaeeee neioaca oei?ii?iecaiaeiuo
1,2- e 1,4-iaooioeiiiia, a oii /enea n i?ino?ainoaaiii-cao?oaeiaiiuie
caianoeoaeyie, n aaieiaeueiuie e aaoa?ioeeeee/aneeie o?aaiaioaie. A
neaaenoaee iieo/aiiuo yenia?eiaioaeueiuo aeaiiuo, i?aaeeiaeaiu noaiu
i?ioio?iiiuo iea?aoeee aoiia aiaei?iaea a oeiieaeiuo nenoaiao n
aeae?iene- e aieiia?oiiaie a ninaaeieo iieiaeaieyo.

Eco/aeanue ?aaeoeeiiiay niiniaiinoue
2,3-aeeaeae?i-3,3-aeeoei?i-1,4-iaooioeiiiia a ?aaeoeeyo n iaeioi?uie
ioeeaioeeueiuie ?aaaaioaie, oaeeie eae a?iiaoe/aneea aieiu, NI-eeneiou,
aeae?aceiu e uaei/e.

?acoeueoaoii acaeiiaeaenoaey aaieiaeueiuo aeeoei?eaeia 1,4-iaooioeiiia n
aieeeiii e oieoeaeeiii yaeythony i?iaeoeou i?eniaaeeiaiey
ioeeaioeeueiiai ?aaaaioa e aeaieiie N=N eee N=I nayce n aaieiaeueiui
aeeoei?eaeiui o?aaiaioii a naiai no?iaiee.

Eco/aiea ?aaeoeee 2-oaieeeieiii?iecaiaeiiai 3,3-aeeoei?iiaooioeiiia n
aeae?aceiaie a oneiaeyo ?aaeoeee Ieoayey i?eaaei e ianeieueei eiui
?acoeueoaoai, a eiaiii, iaaethaeaaony ainnoaiiaeaiea oeeeeiaaenaiiaiai
o?aaiaioa ia?ae/iiai iaooioeiiia. I/aaeaeii, i?ienoiaeeo i?iiaaeooi/iia
ia?aciaaiea aeiii?ii-aeoeaioi?iiai eiiieaena, aaea aeiii?ii aunooiaao
iaooioeiieaeiay no?oeoo?a, aiaei?iae eioi?ie eiaao iaiiaeaeaiioth ia?o
yeaeo?iiia, a aeoeaioi?ii — aoii aiaei?iaea aeae?aceiiie a?oiiu.

Acaeiiaeaenoaea 2,3-aeeaeae?i-3,3-aeeoei?i-2-oaieeeieii-1,4-iaooioeiiia
n NI-eeneioaie a i?enoonoaee o?eyoeaieia, aa?iyoii, i?ienoiaeeo /a?ac
i?iiaaeooi/iia ia?aciaaiea aieii-?aaeeeaea n eiia/iui i?iaeoeoii
ainnoaiiaeaiey iaooioeiieaeiie no?oeoo?u. A neo/aa i?iaaaeaiey ?aaeoeee
NI-eeneiou n 2,3-aeeaeae?i-3,3-aeeoei?i-2-ieni-1,4-iaooioeiiiii eiaao
ianoi i?eniaaeeiaiea e aeaieiie oaea?iae-eenei?iaeiie nayce.

I?ioeann acaeiiaeaenoaey
2,3-aeeaeae?i-3,3-aeeoei?i-2-oaieeeieii-1,4-iaooioeiiia ni uaei/ueth a
nie?oiaie n?aaea i?ienoiaeeo n ia?aa?oiie?iaeie oanoe/eaiiiai
oeiieaeiiai oeeeea e iyoe/eaiiiio ienieiaeaiiaiio; i?e/ai, eiia/iue
i?iaeoeo iiaeao oai?aoe/anee i?aauaaoue a o?ao oi?iao, a neaaenoaee
i?ioio?iiiie iea?aoeee i?ioiia a ienieiaeaiiaii eieueoea.

Enneaaeiaaia aeieiae/aneay aeoeaiinoue neioace?iaaiiuo a
aeenna?oaoeeiiiie ?iaioa aauanoa n oeaeueth iienea eo i?aeoe/aneiai
i?eiaiaiey.

I?e eco/aiee i?ioeaiooaa?eoeaciie aeoeaiinoe iaeaieaa oi?ioea
iieacaoaee, eioi?ua oa?aeoa?ecothony inoaiiaeie ?inoa e ?aciiiaeaiey
ooaiia ieeiaaeoa?ee ooaa?eoeaca i?iyaeee
2,3-aeeaeae?i-3,3-aeeoei?i-2-(4-ieni-3,5-aee-o?ao-aooee-2,5-oeeeeiaaenaa
eeaieeeaeai)-1,4-iaooioeiii, 3,4-
aeeaeae?i-3,3-aeeoei?i-4-(4-ieni-3,5-aee-o?ao-aooee-2,5-oeeeeiaaenaaeeai
eeeaeai)-1,2-iaooioeiii, a oaeaea
2-(4-aeae?iene-3,5-aee-o?ao-aooeeoaiee)-3-(1,2,3-aaicio?eacieee)-1,4-iao
oioeiii. Aunieie ooiaeaaeoa?eoeeaeiie aeoeaiinoueth aeaaeatho aeaa
oaieeeieiii?iecaiaeiuo aaieiaeueiuo aeeoei?eaea (21) e (22), i /ai
naeaeaoaeuenoaoao iiaeaaeaiea ?inoa Aspergillus niger, Fusarium
moniliforme, Venturia inaequolis e oeoiooi?ica oiiaoia. Ii yoei
iieacaoaeyi enneaaeoaiua ia?acoeu i?eaeeaeathony, a a iaeioi?uo neo/ayo
aeaaea i?aainoiaeyo yoaeiiiua i?aia?aou.

Neioace?iaaiiua aieiioei?i?iecaiaeiua 1,4-iaooioeiiia auee eniieueciaaiu
a ea/anoaa aeeacininoaaeythueo i?e iieo/aiee iiauo aee?i?anoai?eiuo
e?aneoaeae, eioi?ua auee ai?iae?iaaiu ia Eaaii-O?aieianeie oe?ia
«Aa?aa».

Eeth/aaua neiaa: iaooioeiii, o?ao-aooeeaeiioei?ieo, aaieiaeueiua
aeeoei?eaeu, ioeeaioeeueiua ?aaaaiou.

Gubriy Z.V. Synthesis and properties of geminalic dichloroderivates of
1,2- and 1,4-naphthoquinones. — Manuscript.

Thesis for a candidate’s degree by speciality 02.00.03 — organic
chemistry. -State University «Lviv polytechnic», Lviv, 1998.

The dissertation is devoted to investigations of synthesis and reactions
of geminalic dichloroderivates of 1,2- and 1,4-naphthoquinones with
nucleophilic reagents; it have been found of new compounds with
practical properties. The 3-chloroderivates are obtained by chloration
with tert-butyl-hypochlorite of derivates of 1,2- and
1,4-naphthoquinones; their next reactions lead to geminalic dichlorides.

The schemes of chemical transformation have been proposed as the attempt
to explain chemical properties of synthesized of 3,3-dichloroderivates
of 1,4-naphthoquinones in reactions with nucleophylic reagents.

Key words: naphthoquinone, tert-butylgypochlorite, geminalic
dichlorides, nucleophylic reagents.

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