IAOe?IIAEUeIA AEAAeAI?ss IAOE OE?A?IE

?INOEOOO I?AAI?*II? O?I??

OAeE 547.241’779 + 547.241’879

AeIAAIIIEEE

Na?a?e ?aaiiae/

NI?ssAEAI? ?IAI?IE A NEIOAC? OINOI?IAI?NIEO AAOA?IOeEEE?A

02.00.08 – o?i?y aeaiaioii?aai?/ieo niieoe

AAOI?AOA?AO

aeena?oaoe?? ia caeiaoooy iaoeiaiai nooiaiy eaiaeeaeaoa o?i?/ieo iaoe

Ee?a – 1998

Aeena?oaoe??th ? ?oeiien.

?iaioa aeeiiaia o a?aeae?e? o?i?? oinoi?ii?aai?/ieo niieoe ?inoeoooo
i?aai?/ii? o?i?? Iaoe?iiaeueii? Aeaaeai?? Iaoe Oe?a?ie.

Iaoeiaee ea??aiee: aeieoi? o?i?/ieo iaoe Oieia/ia Aiae??e Ieaen?eiae/

?inoeooo i?aai?/ii? o?i?? IAI Oe?a?ie, i. Ee?a, noa?oee iaoeiaee
ni?a?ia?oiee

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

Ae?a/ Ai?en Na?a?eiae/, ?inoeooo a?ii?aai?/ii? o?i?? oa iaooio?i??
IAI Oe?a?ie, i. Ee?a, caa?aeoth/ee a?aeae?eii

eaiaeeaeao o?i?/i?o iaoe Aeai/aiei Aiaoie?e Ieoaeeiae/, *a?i?a?anueeee
iaaeaaia?/iee oi?aa?neoao, eaoaae?a o?i??, i.*a?i?a?a, aeioeaio

I?ia?aeia onoaiiaa: Ee?anueeee iaoe?iiaeueiee oi?aa?neoao ?i. Oa?ana
Oaa/aiea, eaoaae?a i?aai?/ii? o?i??, i?i?noa?noai ina?oe, i. Ee?a

Caoeno aeena?oaoe?? a?aeaoaeaoueny “15” ea?oiy 1999 ?. i 14 aiaeei? ia
can?aeaii? niaoe?ae?ciaaiii? a/aii? ?aaee Ae 26.217.01 i?e ?inoeooo?
i?aai?/ii? o?i?? IAI Oe?a?ie ca aae?anith: 252660, Ee?a–94, aoe.
Io?iainueea, 5.

C aeena?oaoe??th iiaeia iciaeiieoenue a iaoeia?e a?ae?ioaoe? ?inoeoooo
i?aai?/ii? o?i?? IAI Oe?a?ie.

Aaoi?aoa?ao ?ic?neaiee “ 12 ” aa?aciy 1999 ?.

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

Aeieoi? o?i?/ieo iaoe, i?ioani? ______________________Oauaiei I.A.

CAAAEUeIA OA?AEOA?ENOEEA ?IAIOE

Aeooaeuei?noue oaie. Na?aae ??cieo aaeocae o?i?? i?aai?/ieo niieoe
oinoi?o, ye? ao?oeeai ?icaeaathoueny a inoaii? aeanyoee?ooy, aecia/ia
i?noea caeia? o?i?y eiai oeeee?/ieo iio?aeieo. Oae, a iiiia?ao?? O.Iaiia
aeaeaiiy 1950 ?ieo, i?enay/ai?e o?i?? aaoa?ioeeee?/ieo iio?aeieo
oinoi?o, a?naio, noea?th ? a?niooo, ?icaeyae oeeee?/ieo niieoe oinoi?o
caeia? o?eueee 15 noi??iie, aea iienaii 11 oeeee?/ieo nenoai. O ae?oaiio
aeaeaii? 1970 ?ieo oe??? iiiia?ao?? aeacaiee ?icae?e caeiaa oaea 351
noi??ieo c iienii 90 aea?aieo oeeee?a ?c 150 a?aeiieo. Ao?oeeaa
c?inoaiiy aeine?aeaeaiue oaeeo oinoi?i?aai?/ieo niieoe i?iaeiaaeo?oueny
aei iaoeo aei?a, ui a?aeia?aaeaii a aaaaoueio iaeyaeao oa a iiiia?ao??
E. Ea?ia, aea caa?oa?oueny iniaeeaa oaaaa ia oeeee?/i? nenoaie c aoiiii
oinoi?o, yeee ca’ycaiee c iaeiei aai aeaiia aoiiaie aoaeaoeth. Oae?
nenoaie aeineoue no?ee? aei a?ae?ie?co ? a?eueoa iaaaaeothoue ca nai?ie
aeanoeainoyie eeane/i? acio- oa n??eiai?ni? aaoa?ioeeeee. Iaeiae aiie
iaei aeinooii? oa iio?aaothoue iniaeeaeo iaoiae?a neioaco.

Ca inoaii? aeenyoee?ooy ?ic?iaeaii c?o/i? iaoiaee Csp2-oinoi?eethaaiiy
aaeiaai?aeaie oinoi?o(III) aeaeo?iiicaaaa/aieo iaiane/aieo niieoe.
Iaea?eueo ?aaeoe?eiicaeaoi? c ieo iathoue o nai?o iieaeoeao ?iai?iiee
o?aaiaio. Aoei oe?eaai aeei?enoaoe oe? iaoiaee oaeiae ? aeey
aaoa?ioeeee?caoe?e iaiane/aieo niieoe aaeiaai?aeaie oinoi?o(III). Aeey
io?eiaiiy i’yoe- /e oanoe/eaiieo iaiane/aieo oinoi?iai?nieo oeeee?a
aeo?aeia i?aai?/ia niieoea iiaeiia iaoe a nai?e iieaeoe? iaiane/aiee
eaioetha c /ioe?ueio aai i’yoe aoii?a, yeee iiaea ii/eiaoeny
aenieiioeeaio?eueiei ?iai?iiei sp2-a?a?eaeeciaaiei (-aoiiii aoaeaoeth, a
cae?i/oaaoeny ?ioei ioeeaio?eueiei oeaio?ii ia aoii? aoaeaoeth aai
acioo. Oaeei /eiii, caaaeueiei o?aaiaioii niieoe, ui oeeee?cothoueny,
aoaea o?aaiaio ?iai?io, eii’thaiaaiee c iiaea?eiei ca’yceii N=N /e N=N,
oiaoi o?aaiaio ni?yaeaiiai ?iai?io. I?iaeoeoaie oaeeo ia?aoai?aiue
iiaeooue aooe oinoi?iai?ni? aaoa?ioeeeee c iaeiei aai aeaiia ca’yceaie
aoaeaoeue-oinoi?. Oiio ?ic?iaeaiiy c?o/ieo iaoiae?a ?o io?eiaiiy ?, ia
iao iiaeyae, aeooaeueiei.

Iaoith ?iaioe ? ?ic?iaeaiiy c?o/ieo iaoiae?a aaoa?ioeeee?caoe?e
aaeiaai?aeaie o?eaaeaioiiai oinoi?o iaiane/aieo i?aai?/ieo niieoe c
o?aaiaioaie ni?yaeaieo ?iai?i?a, a oaeiae aea/aiiy aeanoeainoae
io?eiaieo oinoi?iai?nieo aaoa?ioeeee?a. Ia’?eoaie aeey oeeee?caoe?e ie
aeei?enoaee ?yae aeinooiieo ?iai?iia?ae?acii?a, ?iai?iiaaoa?ee?i?i?a ?
N-a?i?ei??ie?a.

Iaoeiaa iiaecia. Aia?oa iieacaii, ui iaoiaee N-oinoi?eethaaiiy
ni?yaeaieo ?iai?i?a aaeiaai?aeaie o?eaaeaioiiai oinoi?o a i?enooiino?
iniia iiaeooue aooe aeei?enoai? aeey neioaco oe?ieiai ?yaeo
oinoi?iai?nieo i’yoe- oa oanoe/eaiieo aaoa?ioeeee?a, ni?yaeaieo c
?iai?iiei o?aaiaioii. A ?acoeueoao? aaeaeiny ?ic?iaeoe caaaeuei? iaoiaee
neioaco oinoie?i?a ? oino?i?i?a ?c ca’yceii P(III)-Hlg. Ciaeaeaii, ui
?ii?caoe?y ca’yceo P-Hlg 1,2,3-ae?acaoinoie?i?a o ?ic/eiao coiiaeaia
aaaaeaiiyi a neeaae iieaeoe aeaeo?iiiaeiii?iiai o?aaiaioo ?iai?ia.

Ai?iaaoe?y ?iaioe. ?acoeueoaoe ?iaioe aeiiia?aeaeenue ia XIII
I?aeia?iaei?e eiioa?aioe?? c o?i?? oinoi?o (??onaeei, 1995 ?.), XIV
I?aeia?iaei?e eiioa?aioe?? c o?i?? oinoi?o (Oe?ioe?iao?, 1998 ?.), XVII
Oe?a?inuee?e eiioa?aioe?? c i?aai?/ii? o?i?? (Oa?e?a, 1995 ?.), XVIII
Oe?a?inuee?e eiioa?aioe?? c i?aai?/ii? o?i?? (Aei?i?iiao?ianuee, 1998
?.).

Ioae?eaoe??. Ca iaoa??aeaie aeena?oaoe?eii? ?iaioe iioae?eiaaii 4
noaoo?.

No?oeoo?a oa ianya ?iaioe. Aeena?oaoe?y aeeeaaeaia ia 129 noi??ieao ?
neeaaea?oueny ?c anooio, o?ueio ?icae?e?a, aeniiae?a, nieneo e?oa?aoo?e,
ui i?noeoue 89 iaeiaioaaiue. A ?iaio? ? 18 oaaeeoeue.

Ia?oee ?icae?e aeena?oaoe?? i?enay/aiee ocaaaeueiaiith ? aiae?co
iaoiae?a neioaco oinoi?iai?nieo oeeee?a ca ?aaeoe?yie aaeiaai?ae?a
o?eaaeaioiiai oinoi?o c iaiane/aieie niieoeaie, ui i?ioiaeyoue aac ci?ie
aaeaioiino? aoiia oinoi?o. Aeani? aeine?aeaeaiiy aeeeaaeaii a ianooiieo
aeaio ?icae?eao.

A ae?oaiio ?icae?e? a?aeia?aaeai? ?acoeueoaoe aeine?aeaeaiiy ?aaeoe?e
aaeiaai?ae?a o?eaaeaioiiai oinoi?o c ?iai?iia?ae?aciiaie ?
?iai?iiaaoa?ee?i?iaie, ui i?eaiaeyoue aei 1,2,3-ae?acaoinoie?i?a ?
1,3,4-ae?acaoino?i?i?a, oa aea/ai? ?o o?i?/i? aeanoeaino?.

A o?aoueiio ?icae?e? iienai? aaoa?ioeeee?caoe?? aaeiaai?aeaie
o?eaaeaioiiai oinoi?o ?iai?iiaaoa?ee?i?i?a oa N-a?i?ei??ie?a ca o/anoth
aeaio aoii?a aoaeaoeth, ui i?eaiaeyoue aei ooai?aiiy acaoinoie?a,
acaoino?i?i?a ? a?n-oinoi?eeueiaaieo N-a?i?ei??ie?a. A oeueiio ?icae?e?
iienai? oaeiae o?i?/i? aeanoeaino? iiaeo aaoa?ioeeee?a.

Eiie?aoiee iniaenoee aianie aeena?oaioa. Aenia?eiaioaeueia /anoeia
?iaioe, aiae?c niaeo?aeueieo aeine?aeaeaiue oa anoaiiaeaiiy aoaeiae
neioaciaaieo niieoe cae?eniai? iniaenoi caeiaoaa/ai.

INIIAIEE CI?NO ?IAIOE

Aaoa?ioeeee?caoe?? aaeiaai?aeaie oinoi?o(III) ca o/anoth aoii?a
aoaeaoeth oa acioo ni?yaeaieo ?iai?i?a.

O a?aeae?e? o?i?? OIN IAIO iaa?iiaaeaeaii aaeeeee aeina?ae
oinoi?eethaaiiy aoeeee?/ieo ? aaoa?ioeeee?/ieo ?iai?i?a, a oiio /ene?
i?iieneiai aeinooiiiai 1,3,3-o?eiaoee-2-iaoeeai?iaeie?io.
Oinoi?eeueiaai? iio?aei? inoaiiueiai, ye aoei anoaiiaeaii ?ai?oa,
noaa?euei? oa iiaeooue aooe aeae?eai? a ?iaeea?aeoaeueiiio noai?. Iiaeia
aoei i?eionoeoe, ui ? a?eueo neeaaei? oinoi?eeueiaai? iio?aei? oeueiai
?iai?io aoaeooue noaa?eueieie niieoeaie. Oiio ia’?eoaie CPN-oeeee?caoe?e
iaie aoee aea?ai? a?ae?aciie (-oi?i?e-1,3,3-o?eiaoee-2-iaoeeai?iaeie?io
(5), yeee i?noeoue aeaa ioeeaio?euei? oeaio?e – ?iai?iiee aoii aoaeaoeth
oa aoii acioo a?ae?aciiii? a?oie.

?aaeoe?y a?ae?acii?a (5) c o?eoei?eaeii aai o?ea?ii?aeii oinoi?o a
?ic/ei? aeeoei?iaoaio aai i??eaeeio a i?enooiino? o?eaoeeai?io i?e 200N
i?ioiaeeoue ca aeae?eueea oaeeei c ooai?aiiyi ae?acaoinoie?i?a (6,7).
?aaeoe?? a?ae?aciio (5 a) c oai?eaeeoei?oino?iii oa o?iieneaeii
o?eoei?eaeo oinoi?o eaeooue cia/ii iia?euei?oa ? caaa?oothoueny
a?aeiia?aeii ca 24 ? 72 aiaeeie c ooai?aiiyi niieoe (8,9). Oaeei /eiii,
i?iaeoeoe aeacaieo ia?aoai?aiue i?noyoue oeeee 1,2,3-ae?acaoinoie?io,
ni?yaeaiee c ?iai?iiei o?aaiaioii. Ooo ? aeae? neeaae on?o iiaeo niieoe
i?aeoaa?aeaeaii aeaieie yeaiaioiiai aiae?co, a no?oeoo?a –
niaeo?aeueieie aeaieie (ssI? 1I, 31?, 13N) oa o?i?/ieie ia?aoai?aiiyie.
Niaeo?e ssI? 1I,13N ci?iaeeny a CDCl3, ssI? 31? – a aeeoei?iaoai?.

Iiaeia aoei i/?eoaaoe, ui oinoi?eethaaiiy a?ae?aciio (10), ui i?noeoue
aeeiaoeeai?iia?oio, aaeiaai?aeaie o?eaaeaioiiai oinoi?o aoaea i?ioiaeeoe
aeeeth/ii ca o/anoth ?iai?iiiai aoiia aoaeaoeth. Iaeiae aeyaeeinue, ui
a?ae?acii (10) i?aeoe/ii ieoo?ai ?aaao? c o?ea?ii?aeii oinoi?o a ?ic/ei?
i??eaeeio c ooai?aiiyi ae?acaoinoie?io (11). Oaeei /eiii, a oeueiio
aeiaaeeo N-oinoi?eethaaiiy ?iai?iiiai o?aaiaioa noi?iaiaeaeo?oueny
a?aeuaieaiiyi iaoeeueii? a?oie a?ae aoiia acioo, ui iae?iia??i?oa
iiynith?oueny aenieith aia?aaoe/iith aea?aei?noth ooai?aiiy
ae?acaoinoie?iiaiai oeeeeo.

Ne?ae cacia/eoe, ui ia a?aei?io a?ae oeeee?caoe?e c ooai?aiiyi
1,2,3-ae?acaoinoie?a, i?iaaaeaieo ?ai?oa Oaaoeiaei-Oeeianueeei oa
Oi?aeiaoa?ii, o iao?e ?iaio? aia?oa ?ic?iaeaii iaoiaee io?eiaiiy
1,2,3-ae?acaoinoie?i?a, o oiio /ene? c? ca’yceii P-Hlg.

Ae?acaoinoie?ie-P(III) (6, 7, 11), — e?enoae?/i? niieoee, noaa?euei? ca
a?aenooiino? aieiae iia?o?y. Cie?aia, ye ? ?io? P-Hlg iio?aei?, aiie
anooiathoue a ?aaeoe??, ui ? oa?aeoa?ieie aeey aaeiaaiaia?ae?eae?a
o?eaaeaioiiai oinoi?o c ooai?aiiyi niieoe (12). Inoaii? eaaei
ia?aoai?ai? cae/aeieie iaoiaeaie a noaa?euei? ae?acaoinoie?ie-P(V) (13).

A?ae?ie?c niieoe (6, 7, 11) i?eaiaeeoue aei oeeee?/ieo
a?ae?ioinoi?eeueieo iio?aeieo (14). Iiae?aii aei ?ioeo aaeiaaioino?i?a c
aeaeo?iiiaeiii?iith 2-iaoeeai?iaeie?iiaith a?oiith niieoea (11) eaaei
?aaao? c n??eith c ooai?aiiyi o?iieneaeo (15).

Neaiaee aoii?a oinoi?o ae?acaoinoie?i?a (11) o aaicie? oa aeeoei?iaoai?
cao?eniaai? a?aeiia?aeii a iaeano? 160 oa 225 i.ae. Iecueeiiieueia
cia/aiiy o?i?/iiai cnoao neaiaeo aoiia oinoi?o a ?ic/ei? aeeoei?iaoaio
oa?aeoa?ia aeey niieoe aeaieii?aeeiiaaiiai oinoi?o oa na?ae/eoue i?i
aeenioe?aoe?th niieoee (11) a ?ic/ei? c ooai?aiiyi ai?iio a?iio oa
eao?iio ae?acaoinoieo (11 a). Aeey ia?aa??ee oeueiai i?eiouaiiy iaie
aoei neioaciaaii n?eue (16), yea, iica anyeei noii?aii, ? ?iiiith
niieoeith. Neaiae aoiia oinoi?o ae?acaoinoieo (16) a aeeoei?iaoai?
ciaoiaeeoueny i?e 242.7 i.ae., ui i?aeoaa?aeaeo? c?iaeaia aeua
i?eiouaiiy. Oaeei /eiii, ia? i?noea eaaea aca?iiia?aoai?aiiy aeaio oei?a
niieoe oinoi?o c eii?aeeiaoe?eieie /eneaie 2 ? 3, oiaoi yaeua
eii?aeeiaoe?eii? ?ciia??? niieoe oinoi?o. A caeaaeiino? a?ae i?e?iaee
?ic/eiieea oey ??aiiaaaa iiaea ci?uoaaoeny a a?e eiaaeaioii? aai ?iiii?
oi?ie.

A niaeo?ao ssI? 31? a ??cieo ?ic/eiieeao neaiaee aoiia oinoi?o
ae?acaoinoie?i?a (6,7) c oai?eueiei cai?nieeii a?ey aoiia acioo
ciaoiaeyoueny a iaaeao 150 i.ae., oiaoi a iaeano?, oa?aeoa?i?e aeey
eiaaeaioii? oi?ie.

Ia?aoai?aiiy oei?oinoie?io (6 a) oa a?iioinoie?io (7) a ae?acaoinoiee
(17 a,b) eaaei i?ioiaeeoue i?e ae?? ia ieo oao?aoai?eai?aoo iao??th aai
o?eiaoeenee?eo?eooi?iaoainoeueoiiaoo.

Oaeei /eiii, ?ii?caoe?y ca’yceo P-Hlg a ae?acaoinoie?iao cia/iith i??ith
caeaaeeoue ye a?ae i?e?iaee cai?nieea a?ey aoiia acioo, oae ? a?ae
i?e?iaee ?ic/eiieea.

Ae?acaoinoie?ie (13) c i’yoeaaeaioiei aoiiii oinoi?o – no?ee?
e?enoae?/i? niieoee ? iiaeooue aooe aaaaeai? a aeaye? ?aaeoe??
aeaeo?io?eueiiai cai?uaiiy. Ae?acaoinoie?i (13 a) eaaei i?o?ico?oueny
i?e 20 iN a ?ic/ei? ioeoiai? eeneioe ii aciiaoeiiaiio aoiio aoaeaoeth,
aea ia a?iio?oueny i?e e?iiaoi?e oaiia?aoo??. Niieoea (13 b) ia a?aei?io
a?ae (13 a) i?o?ico?oueny a oeo naieo oiiaao a ia?a-iieiaeaiiy
oai?eueiiai yae?a oa a?iio?oueny a i’yeeo oiiaao a aeaa iieiaeaiiy —
ia?a-iieiaeaiiy oai?eueiiai yae?a oa iieiaeaiiy 5 ?iaeie?iiaiai
o?aaiaioa.

A ?yaeo neioaciaaieo ae?acaoinoie?i?a iiaeia aoei i/?eoaaoe iayai?noue
aeaio aaiiao?e/ieo ?ciia??a (A oa A), aea iciae ?ciia??? a niaeo?ao ssI?
aeine?aeaeaieo niieoe ia aeyaeaii. Aea?? ia ei?enoue ?ciia?o (A) iaie
aoei c?iaeaii ia iniia? eaioaii?aeieo ?iaeoeiaaieo cnoa?a (E?C) a
niaeo?ao II? ae?acaoinoie?i?a, aeeeeeaieo eaioaii?aeiei cnoaiei
?aaaaioii – eiiieaenii ?a?ii?th (Eu(fod)3), a oaeiae ?o ?ic?aoiaaieo
cia/aiue.

Ie aaaaea?ii, ui ?ciia? A iaeiaio i?inoi?iai oo?oaeiaiee ? oiio
iaea?eueo eiia??iee.

A?aei?iiith iniaeea?noth iieaeoe ae?acaoinoie?i?a, iienaieo aeua, ?
iayai?noue a ?o neeaae? aeiii?iiai ?iai?iiiai cai?nieea, caeaoiiai aei
ni?yaeaiiy c oeeeeii ae?acaoinoie?io. Iaeiae iniiai?noue aoiia acioo,
iayaiiai a ?iaeie?iiaiio o?aaiaio?, cia/ii iineaaeaia. Aoei aeioe?eueii
neioacoaaoe oa aeine?aeeoe aeanoeaino? niieoe c a?eueo iniiaiei
?iai?iiei o?aaiaioii. Aeey cae?eniaiiy CPN-oeeee?caoe?e iaie neioaciaai?
oeeee?/i? ?iai?iia?ae?aciie (21 a-d) c caeeoeaie i?ia?eaeeio, ii?oie?io
oa i??ie?aeeio. A?aecia/eii, ui iaea?eueo iniiaiei na?aae caaaeaieo ?
caeeoie i??ie?aeeio.

I?e aca?iiae?? o?eoei?eaeo aai o?ea?ii?aeo oinoi?o c a?ae?aciiaie
(21 a-d) io?eiaii e?enoae?/i? oao?aa?ae?iaaiciae?acaoinoie?ie (22 a-d,
24) no?ee? aac aeinooio aieiae iia?o?y. ?aaeoe?y i?io?ea? a ?ic/ei?
aeeoei?iaoaio aai i??eaeeio, a i?enooiino? o?eaoeeai?io ? i?e e?iiaoi?e
oaiia?aoo?? caaa?oo?oueny ca aeae?eueea oaeeei.

A niaeo?ao ssI? 31P ae?acaoinoie?io (22 n), ui i?noeoue caeeoie
i??ie?aeeio, a ?ic/eiao aeeoei?iaoaio oa oieoieo neaiaee aoii?a oinoi?o
ciaoiaeyoueny a?aeiia?aeii i?e 172.0 i.ae. ? 123.8i.ae., ui na?ae/eoue
i?i iayai?noue o ?ic/ei? aeaio ?ciia??a (22 n) oa (23), c aoiiaie
oinoi?o ??cii? eii?aeeiaoe??.

Niieoee (22 a,b), ui i?noyoue caeeoee i?ia?eaeeio oa ii?oie?io, noaey/e
c niaeo??a ssI? 31P, iathoue eiaaeaioio aoaeiao o an?o ?ic/eiieeao.
Oaeei /eiii, caeeoie i??ie?aeeio ia? iaeneeuei?oee aeaeo?iiiaeiii?iee
aieea ia i?ioean ?ii?caoe?? ca’yceo P-Cl, iacaaaeath/e ia iayai?noue
aeoeaioi?iiai oai?eueiiai cai?nieea a?ey aoiia acioo. ?acii c oei, a
niaeo?ao ssI? 31? a?iiae?acaoinoie?io (24) a ?ic/ei? aaicieo
niinoa??aa?oueny neaiae aoiia oinoi?o i?e 151i.ae., a a aeeoei?iaoai? oa
oei?ioi?i? — i?e 210i.ae., ui na?ae/eoue i?i ae?acaoinoieueio no?oeoo?o
(25) a oeeo ?ic/eiieeao. Ca?aene iiaeia c?iaeoe aeniiaie, ui ca?eueoaiiy
iniiaiino? ?iai?iiiai acioo oa ioeeaiooaiino? aaeiaaio ni?ey? ?ii?caoe??
ca’yceo P-Hlg a iieaeoeao ae?acaoinoie?i?a.

I?e ae?? aea?iiey?ii? e?eueeino? o?eaoeeai?io ia aaeiaaiaia?ae?eaee
(22 a,b) io?eiaii noaa?euei? aeea?ae?iaaiciae?acaoinoiee (26 a,b) c
oa?aeoa?iei neaiaeii a?oie =NI- a niaeo?? II? i?e (I=4.6 i.ae. A
niaeo?ao ssI? 31P ae?acaoinoie?a (26 a,b), a ?ic/ei? aaicieo,
cao?eniaaii neaiaee aoiia oinoi?o i?e 229,7 i.ae. oa 201,6 i.ae.,
a?aeiia?aeii.

Ae?acaoinoie?ie (22) eaaei ia?aoai?ai? cae/aeieie iaoiaeaie a
noaa?euei? oeeee?/i? niieoee c i’yoeaaeaioiei aoiiii oinoi?o (27-29).

Cai?iiiiiaaiee iaie iaoiae CPN-oeeee?caoe?e oaeiae aeyaeany i?eeiyoiei
aeey io?eiaiiy oanoe/eaiieo oinoi?iai?ni?o aaoa?ioeeee?a.

Aaoa?ee?i?ie (30, 31), ui i?noyoue ?iai?iiee aoii aoaeaoeth oa
NH-a?oio acioiai?niiai aaoa?ioeeeea, ?aaaothoue c oai?eaeea?iioino?iii
aai oai?eaeeoei?oino?iii a ?ic/ei? aeeoei?iaoaio a i?enooiino?
o?eaoeeai?io c ooai?aiiyi ae?acaoino?i?i?a (32, 34), ye? eaaei
ia?aoai?aii a noeueo?aee (33, 35). Iniaeeaith a?aei?ii?noth niieoe (32
-35), ui i?noyoue oanoe/eaiiee oinoi?iai?niee oeeee, ? iayai?noue a
iueiio a?oie NH oa iiaiai ?iai?iiiai o?aaiaioa.

Oaeei /eiii, aia?oa neioaciaai? aaoa?ioeeeee ?yaeo
1,3.4-ae?acaoino?i?io, ye? eiiaeainiaai? c i’yoe/eaiiei acioiai?niei
aaoa?ioeeeeii ? oeeeeiaaenaiii.

2. Aaoa?ioeeee?caoe?? aaeiaai?aeaie oinoi?o(III) ca o/anoth aeaio aoii?a
aoaeaoeth ni?yaeaieo ?iai?i?a.

Cai?iiiiiaaiee iaoiae aaoa?ioeeee?caoe?e aoei aeei?enoaii oaeiae aeey
neioaco oinoi?iai?nieo aaoa?ioeeee?a c aeaiia N-? ca’yceaie. A
N?N-oeeee?caoe?? aaaaeaii ni?yaeai? ?iai?ie (36), ae?oaei ioeeaio?eueiei
oeaio?ii yeeo ? iieiaeaiiy 4 i??acieueiiai oeeeeo.

I?e ?o aca?iiae?? c o?ea?ii?aeii aai o?eoei?eaeii oinoi?o a
aeeoei?iaoai? oa a i?enooiino? iniia ooai?ththoueny no?ee? aac aeinooio
aieiae iia?o?y aeea?ae?ii??aciei-1,4-acaoino?i?ie (37 a-n). Ne?ae
cacia/eoe, ui 1-oai?e-3,5-aeeiaoeei??aciee ia oinoi?eeththoueny
o?eoei?eaeii oinoi?o, oiio ioeeaio?euei?noue iieiaeaiiy 4 a
i??acieueiiio yae?? niieoee (36), eiia??ii, i?aeaeuaia ca ?aooiie
ni?yaeaiiy c ?iai?iiei caeeoeii.

Aca?iiae?y niieoee (36) c iaio aeoeaieie aaeiaai?aeaie oinoi?o(III) —
oai?eaeea?iioino?iii ? oai?eaeeoei?oino?iii — i?ioiaeeoue a oaeeo naieo
oiiaao, aea iia?euei?oa, c ooai?aiiyi niieoe (38 a,b).

Caoaaaeeii, ui aeioaia? aoee a?aenooi? iaoiaee io?eiaiiy
1,4-acaoino?i?i?a c? ca’yceii P-Hlg.

Ia a?aei?io a?ae P-Hlg ae?acaoinoie?i?a, niieoee (37 a-n) ia
ooai?ththoue eao?ii?a 1,4-acaoino?i?i?a iaa?oue i?e ia?iaoe?
oao?aoai?eai?aoii iao??th. Oeeee?/i? aaeiaaiaia?ae?eaee (37 a,b)
cae/aeieie iaoiaeaie eaaei ia?aoai?ththoueny a niieoee c i’yoeaaeaioiei
aoiiii oinoi?o (39, 40). Oeeee?/i? i?aai?eoino?ie (38 a,b) eaaei
ieeniththoueny ia?ieneaeii aiaeith, a?eeaceaeaie, a oaeiae n??eith c
ooai?aiiyi a?aeiia?aeieo iio?aeieo (41).

Aaiiao??y niieoe (36-41) aaccaia?a/ii aeiaaaeaia caaaeyee aeei?enoaiith
niaoe?aeueieo iaoiaeee i?e caien? ssI? niaeo??a, a naia niaeo?ineii?? ia
iniia? yaea?iiai aoaeoo Iaa?oaoca?a. A oi?ioeao (36 — 41) ia noai?
no??eeaie cia?aaeaii a?oie, aeey yeeo cao?eniaaia iaea?eueoa yaea?ia
aca?iiae?y, ui niinoa??aa?oueny a niaeo?ao II?.

Aoei oe?eaai aaanoe a N?N-oeeee?caoe?? niieoee c iaei?ino?oei ?iai?iiei
o?aaiaioii >N-CH=CH2. Aeoiaey/e ?c ?acoeueoao?a iaoeo iiia?aaei?o
aeine?aeaeaiue iiaeia aoei i?eionoeoe, ui aeey io?eiaiiy no?eeeo
i?iaeoeo?a oeeee?caoe?e iaiao?aeii, uia aoii acioo oeueiai o?aaiaioa
aoiaeea aei neeaaeo aaoa?ioeeeeo, yeee eaaei oinoi?eeth?oueny. Oiio aeey
cae?eniaiiy aaoa?ioeeee?caoe?e oaeiai oeio iaie aoee aea?ai?
N-a?i?ei??iee, iaea?eueo aeinooiieie c yeeo ? 2,3-aeecai?uai? iio?aei?
(42). I?e aca?iiae?? N-a?i?ei??ie?a (42 a,c) n o?eoei?eaeii aai
o?ea?ii?aeii oinoi?o a ?ic/ei? aeeoei?iaoaio aai i??eaeeio oa a
i?enooiino? o?eaoeeai?io, i/aaeaeii, ooai?ththoueny oeeee?/i? i?iaeoeoe
oinoi?eethaaiiy, ye? aaea?oueny cao?enoaaoe o?eueee c aeiiiiiaith
niaeo??a ssI? 31?, ine?eueee aiie aeoaea eaaei iie?ia?ecothoueny iaa?oue
i?ney ia?aoai?aiiy a iio?aei? c iyoeaaeaioiei aoiiii oinoi?o.

Ie i?eionoeee, ui iio?aei? N-a?i?ei??ieo c ia’?iiei cai?nieeii a oeeee?
aoaeooue iaio noeeuei? aei iie?ia?ecaoe??. Ae?enii, i?e aca?iiae??
N-a?i?ei??ieo (42 b), ui i?noeoue o?ao-aooeeueio a?oio, c noi?ooth
o?ea?ii?aeo oa o?eoei?eaeo oinoi?o a i??eaeei? o ni?aa?aeiioaii? 2:1 oa
a i?enooiino? o?eaoeeai?io ooai?th?oueny i??ieiacaoinoie?i-P(III) (44).
Oeeee?/iee oei?aia?ae?eae (44) iano?eeee ? oiio eiai ia?aoai?aii a
i??ieiacaoinoie?i- P(V) (45).

Aaoa?ioeeee?caoe?y N-a?i?ei??ie?a (42 a,c) c oai?eaeea?ii- aai
oai?eaeeoei?oino?iii i?ioiaeeoue i?e o?eaaeiio (aei aeaio oeaei?a)
aeo?eioaaiith ?aaeoe?eii? noi?o? i?e 20IN. Iano?ee? oino?ie (46 a,c)
ia?aoai?aii cae/aeieie iaoiaeaie a noaa?euei? niieoee (47
a,c; 48 a).

Aca?iiae?th yea?iiey?ieo e?eueeinoae N-a?i?ei??ieo (42 a) oa
o?eoei?eaeo oinoi?o iiaeia coieieoe ia noaae?? ooai?aiiy aeeoei?oino?io
(49), yeee cao?eniaaii niaeo?ii ssI? 31? oa aeae?eaii ye o?ioinoiiao
(50).

O?ioinoiiao (50) a ?ic/ei? i??eaeeio aca?iiae?? c yea?iiey?iith
e?euee?noth o?ea?ii?aeo oinoi?o a i?enooiino? o?eaoeeai?io c ooai?aiiyi
aeea?iiaia?ae?eaeo (51), a niaeo?? ssI? 31? yeiai ? aeaa neaiaee i?e
150,7 i.ae. oa 60,7 i.ae.). Inoaii?e aeae?eaii a aeaeyae? o?ioinoiiaoo
(52).

Ca’ycie i?ae aeea?iioino?iia?oiith oa aoiiii aoaeaoeth a niieooe? (51)
aeyaeany aeoaea eaa?eueiei, ? iaa??aaiiy ?ic/eio oe?a? niieoee a
i?enooiino? a?iia?ae?aoo i??eaeeio i?eaiaeeoue aei ooai?aiiy aeo?aeiiai
o?ioino?iaoo (50).

AENIIAEE

1. ?ic?iaeaii iaoiaee io?eiaiiy ni?yaeaieo ?iai?i?a ia iniia?
(-oi?i?e-1,3,3-o?eiaoee-2-iaoeeai?iaeie?io oa oeeee?/ieo 1,3-aeeeaoii?a
– ?iai?iia?ae?acii?a oa ?iai?iiaaoa?ee?i?i?a.

2. Iieacaii, ui ?iai?iia?ae?aciie eaaei aca?iiae?thoue c aaeiaai?aeaie
o?eaaeaioiiai oinoi?o a i?enooiino? iniia c ooai?aiiyi oinoi?iai?nieo
i’yoe/eaiieo oeeee?/ieo niieoe ?yaeo 1,2,3-ae?acaoinoie?io.

3. Ciaeaeaii, ui ni?yaeai? c ?iai?iiei caeeoeii 1,2,3-ae?acaoinoie?ie c
o?aaiaioii P-Hlg, a ?ic/eiao iiaeooue ciaoiaeeoenue o oi?i? aeaio
?ciia??a c eii?aeeiaoe?eieie /eneaie aoiia oinoi?o 2 oa 3. Iieiaeaiiy
??aiiaaae caeaaeeoue a?ae i?e?iaee ?ic/eiieea, aeiii?ieo aeanoeainoae
?iai?iiiai o?aaiaioa oa oa?aeoa?o cai?nieea a ae?acaoinoie?iiaiio
oeeee?.

4. Iieacaii, ui a?aeiia?aei? ?iai?iiaaoa?ee?i?ie eaaei aca?iiae?thoue c
aaeiaai?aeaie o?eaaeaioiiai oinoi?o a i?enooiino? iniia c ooai?aiiyi
oinoi?iai?nieo oanoe/eaiieo oeeee?/ieo niieoe ?yaeo
1,3,4-ae?acaoino?i?io oa 1,4-acaoino?i?io, eiiaeainiaaieo c
aaoa?ioeeeeaie aeo?aeii? niieoee (o?eacie, i??acie).

5. Anoaiiaeaii, ui a oanoe/eaiieo oeeee?/ieo niieoeao ?yaeo
1,4-acaoino?i?io ?c ca’yceii P-Hlg ia aaea?oueny a?aeuaieoe ai?ii
aaeiaaio c ooai?aiiyi oanoe/eaiiiai oeeeeo c aeaieii?aeeiiaaiei aoiiii
oinoi?o.

6. Iieacaia iiaeeea?noue N?N-oeeee?caoe?e N-a?i?ei??ie?a aaeiaai?aeaie
o?eaaeaioiiai oinoi?o ii iieiaeaiith 2 i??ieueiiai e?eueoey ? ii
a?i?euei?e a?oi? iaeii/anii c ooai?aiiyi 1,3-acaoinoie?i?a.

7. Ciaeaeaii oiiae oinoi?eethaaiiy N-a?i?ei??ie?a, i?e yeeo io?eiaii
a?n-oinoi?eeueiaai? iio?aei? ii iieiaeaiith 2 i??ieueiiai e?eueoey ? ii
(-aoiio aoaeaoeth a?i?eueii? a?oie.

INIIAIEE CI?NO AeENA?OAOe?? AEEEAAeAII O OAEEO

?IAIOAO

1. Oieia/aa A.A., Aaae/aiei E.I., Aeiaaiiieue N.E., Aieiae A.A.
Aaoa?ioeeeeecaoeee ia iniiaa aeae?aciiia
1,3,3-o?eiaoee-(-oi?iee-2-iaoeeaieiaeieeia // OAN. — 1994. — N.7. — N.
915-918.

2. Tolmachev A.A., Merculov A.S., Dovgopoly S.I., Oshovskiy G.V.,
Pinchuk A.M. C-Phosphorylation of compounds with the electron-rich
double carbon-nitrogen bond // Phosph. Sulf. and Silicon. — 1996. — Vol.
111. — N 1-4. — P. 145.

3. Tolmachev A.A., Dovgopoly S.I., Kostyuk A.N., Kozlov E.S., and
Pushechnikov A.O. Phosphorus-Containing Heterocyclic Compounds Derived
from N-Vinilpyrroles // Heteratom Chemistry –V.8. –N.6. –P.495-499.

4. Tolmachev A.A., Dovgopoly S.I., Kostyuk A.N., Komarov I.V. and
Pinchuk A.M. Phosphorylation of enaminehydrazones as an efficient route
to Diazaphospholines and Diazaphospholes // Phosph. Sulf. and Silicon. —
1997. — Vol. 123. — P. 125-140)

5. Tolmachev A.A., Ivonin S.P., Chaikovskaya A.A., Dovgopoly S.I.,
Pynchuk A.M. C-Phosphorylated Pyrroles and Indoles. // Proc. XIII-th
International Conferenc on Phosphorus Chemistry. –Jerusalem(Israel).
–1995. –P.197.

6. Oieia/aa A.I., Ia?eoeia A.N., Aeiaaiiieee N.?., Eiceia A.N.
N-oinoi?eethaaiiy niieoe, ui iathoue iiaea?eiee caycie aoaeaoeue-acio,
a?ii?aeaie o?eaaeaioiiai oinoi?o. // Oace aeiiia?aeae XVII Oe?a?inueei?
eiioa?aioe?? c i?aai?/ii? o?i??. –Oa?e?a. -1995. –N.286.

7. Kostyuk A.N, Lysenko N.V, Dovgopoly S.I., Tolmachev A.A.
Phosphorylation of Conjugated Enamines. // Proc. XIV-th International
Conferenc on Phosphorus Chemistry. –Cincinnati(USA). –1998. –P.274.

8. Iooa/i?eia I.I., Aeiaaiiieee N.?., Einothe I.I. Iia? aiaeueiaai?
oinoiiia? oa oino?iia? oeeee?/i? ao??e. // Oace aeiiia?aeae XVIII
Oe?a?inueei? eiioa?aioe?? c i?aai?/ii? o?i??. –Aei?i?iiao?ianuee. -1998.
–N.71.

AIIOAOe??

Aeiaaiiieee N. ?. Ni?yaeai? ?iai?ie a neioac? oinoi?iai?nieo
aaoa?ioeeee?a. –?oeiien.

Aeena?oaoe?y ia caeiaoooy iaoeiaiai nooiaiy eaiaeeaeaoa o?i?/ieo iaoe ca
niaoe?aeuei?oueth 02.00.08 – o?i?y aeaiaioii?aai?/ieo niieoe. –?inoeooo
i?aai?/ii? o?i?? Iaoe?iiaeueii? Aeaaeai?? Iaoe Oe?a?ie, Ee?a, 1998.

Caoeua?oueny 4 iaoeia? ?iaioe, i?enay/ai? neioaco oinoi?iai?nieo
aaoa?ioeeee?a ?yaeo 1,2,3-ae?acaoinoie?io, 1,3,4-ae?acaoino?i?io,
1,4-acaoino?i?io oa 1,3-acaoinoie?io, ae??th aaeiaai?ae?a oinoi?o(III)
ia ni?yaeai? ?iai?ie.

Eeth/ia? neiaa: ni?yaeai? ?iai?ie, 1,2,3-ae?acaoinoie?ie,
1,3,4ae?acaoino?i?ie, 1,4-acaoino?i?ie oa 1,3-acaoinoie?ie.

Aeiaaiiieue N. E. Nii?yaeaiiua aiaieiu a neioaca oinoi?niaea?aeaueo
aaoa?ioeeeeia. –?oeiienue.

Aeenna?oaoeey ia nieneaiea o/aiie noaiaie eaiaeeaeaoa oeie/aneeo iaoe ii
niaoeeaeueiinoe 02.00.08 – oeiey yeaiaioii?aaie/aneeo niaaeeiaiee.
–Einoeooo i?aaie/aneie oeiee Iaoeeiiaeueiie Aeaaeaiee Iaoe Oe?aeiu,
Eeaa, 1998.

Caueuaaony 4 iao/iua ?aaiou, iinayuaiiua neioaco oinoi?niaea?aeaueo
aaoa?ioeeeeia ?yaea 1,2,3-aeeacaoinoieeia, 1,3,4-aeeacaoinoeieia,
1,4-acaoinoeieia e 1,3-acaoinoieeia, aeaenoaeai aaeiaaieaeia
oinoi?a(III) ia nii?yaeaiiua aiaieiu.

Eeth/aaua neiaa: nii?yaeaiiua aiaieiu, 1,2,3-aeeacaoinoieeiu,
1,3,4-aeeacaoinoeieiu, 1,4-acaoinoeieiu e 1,3-acaoinoieeiu.

Dovgopoly S.I. Conjugated enamines in synthesis of phosphorus-containing
heterocycles. -Manuscript.

Dissertation for scintific degree of Candidate of Sciences (Chemistry)
in speciality 02.00.08 –elementoorganic chemistry. Institute of Organic
Chemistry, Nathional Academy of Sciences of Ukraine, Kiev, 1998.

4 Scientific works devoted to synthesis of phosphorus-containing
heterocycles of 1,2,3-diazaphospholine, 1,3,4-diazaphosphinine,
1,4-azaphosphinine, and 1,3-azaphospholine types by treating conjugated
enamines with phosphorus(III) halides are defended.

Key words: conjugated enamines, 1,2,3-diazaphospholines,
1,3,4-diazaphosphinines, 1,4-azaphosphinines, and 1,3-azaphospholines.

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