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

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

Ia i?aaao ?oeiieno

OAeE 547.753.241

AI?UAIEI

Aiae??e Ieaenaiae?iae/

N-Oinoi?eeueiaai? iio?aei? 2-oo?ee-,

2-o??i?e- ? 2-(N-iaoeei??ie?e)ea?aaeueaeaa?ae?a

02.00.03- i?aai?/ia o?i?y

AAOI?AOA?AO

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

Ee?a- 1999

Aeena?oaoe??th ? ?oeiien.

Aeena?oaoe??th ? ?oeiien.

?iaioa aeeiiaia ia eaoaae?? i?aai?/ii? o?i??
Aei?i?iiao?ianueeiai

aea?aeaaiiai oi?aa?neoaoo

Iaoeiaee ea??aiee: eaiaeeaeao o?i?/ieo iaoe Eo?i/e?i Ieaenaiae?
Oaaei?iae/

Aei?i?iiao?ianueeee aea?aeaaiee oi?aa?neoao,

caa?aeoth/ee eaoaae?ith o?i?? oa oaoiieia?? AIN

Io?oe?ei? iiiiaioe: Aieiaaiei THe?ai Ieoaeeiae/, Ee?anueeee
Iaoe?iiaeueiee

oi?aa?neoao ?i. O.A.
Oaa/aiea, eaoaae?a i?aai?/ii? o?i??

aeieoi? o?i?/ieo iaoe

Iienueei Iao?i Iao?iae/, ?inoeooo
i?aai?/ii?

o?i?? IAI Oe?a?ie,
i.Ee?a, noa?oee iaoeiaee

ni?a?ia?oiee, eaiaeeaeao
o?i?/ieo iaoe

I?ia?aeia onoaiiaa: Aeiiaoeueeee ?inoeooo o?ceei-i?aai?/ii? o?i?? oa

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

a?aeae?e o?i?? acie?a

Caoeno aeena?oaoe?? a?aeaoaeaoueny “___21__”
_______aeiaoiy___________ 1999 ?.

i __14__ aiaeei? ia can?aeaii? niaoe?ae?ciaaii? 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?neaie? “___17__” _______aa?aniy__________ 1999 ?.

A/aiee nae?eoa? niaoe?ae?ciaaii? ?aaee

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

Aeooaeuei?noue oaie. O?i?y N-oinoi?eeueiaaieo i SYMBOL 162 \f «Symbol»
\s 14 c yoe/eaiieo aaoa?ioeeee?/ieo niieoe ?icaeaa?oueny inoaii?i /anii
aeoaea oaeaeei. Iaineaaiee ?ioa?an aei o?i?? oeeo niieoe iiynith?oueny
?o aenieith a?ieia?/iith aeoeai?noth, iiaeeeaei aeei?enoaiiyi ?o a
eaoae?oe/ieo i?ioeanao oa a i?aia?aoeai?e o?i?? oinoi?i?aai?/ieo niieoe,
a oaeiae ?o oai?aoe/iei cia/aiiyi.

Ii?yae c eeane/ieie iaoiaeaie io?eiaiiy oeeo niieoe, oiaoi
oinoi?eethaaiiyi iaoaeueiaaieo aaoa?ioeeee?a oa oeeee?caoe??th
aoeeee?/ieo oinoi?iai?nieo niieoe, ana a?eueo aaaiiei noa? iaoiae
i?yiiai oinoi?eethaaiiy, yeee aeey SYMBOL 112 \f «Symbol» \s 14 p
-iaaeeeoeiaeo a?iiaoe/ieo aaoa?ioeeee?a aoa ?ic?iaeaiee o a?aeae?e?
o?i?? oinoi?i?aai?/ieo niieoe ?inoeoooo i?aai?/ii? o?i?? IAI Oe?a?ie
?acii c eaoaae?ith i?aai?/ii? o?i?? Aei?i?iiao?ianueeiai aea?aeaaiiai
oi?aa?neoaoo.

Aaaeeeaei iai?yieii a iiaeaeueoiio ?icaeoeo oeueiai iaoiaeo ? io?eiaiiy
ooieoe?iiaeueiicai?uaieo oinoi?ai?nieo niieoe.

Aei ia?niaeoeaieo aeo?aeieo ?aaaaio?a, ye? iathoue aaaeeeaa cia/aiiy
aeey neioaco N-oinoi?eeueiaaieo aaoa?ioeeee?a, ia?o ca ana
ne?ae a?aeianoe N-oinoi?eeueiaai? aeueaeaa?aee SYMBOL 112 \f «Symbol»
\s 14 p -iaaeeeoeiaeo aaoa?ioeeee?a. Oae? niieoee aeoaea iaei aea/ai? ?
a e?oa?aoo?? iienai? eeoa o? c ieo, ye? i?noyoue a aaoa?ioeeee?
o?eoai?eoinoii??ao oa oi?i?eueio a?oie.

A?oiooth/enue ia neacaiiio, iiaeia noaa?aeaeoaaoe, ui aea/aiiy
oinoi?eethaaiiy a?ae?acii?a aeueaeaa?ae?a SYMBOL 112 \f «Symbol» \s 14
p -iaaeeeoeiaeo aaoa?ioeeee?a c iiaeaeueoith ?aaaia?aoe??th
ea?aii?eueii? a?oie oa io?eiaiiy N-oinoi?eeueiaaieo aeueaeaa?ae?a, ? a
iao /an aeooaeueiei.

Iaoith ?iaioe ? neioac iiii- oa a?noinoi?eeueiaaieo aeueaeaa?ae?a
SYMBOL 112 \f «Symbol» \s 14 p -iaaeeeoeiaeo a?iiaoe/ieo aaoa?ioeeee?a c
aeei?enoaiiyi a?ae?aciiiiai caoenoo aeey aeueaeaa?aeii? ooieoe??,
aea/aiiy aieeao N,N-aeeiaoeea?ae?aciiii? a?oie ia ?aaeoe?th i?yiiai
oinoi?eethaaiiy SYMBOL 112 \f «Symbol» \s 14 p -iaaeeeoeiaeo
aaoa?ioeeee?a.

Iaoeiaa iiaecia. Iieacaia ?aa?inaeaeoeai?noue ia?aa?ao ?aaeoe??
oin-oi?eethaaiiy a?ae?acii?a oo?oo?ieo, 2-o??i?e- oa
2-i??ie?eea?aaeueaeaa?-

ae?a oa iiaeeea?noue ?o i?aia?aoeaiiai aeei?enoaiiy aeey io?eiaiiy iiii-
oa a?noinoi?eeueiaaieo iio?aeieo aeacaieo aaoa?ioeeee?a.

Aeyaeaii aoaeo cia/ii? aeoeaaoe?? i??ieo, oo?aio oa o?ioaio
N,N-aee-iaoeea?ae?aciiiith a?oiith a ?aaeoe?? oinoi?eethaaiiy, ui
aeicaiey? aaiaeeoe a i SYMBOL 162 \f «Symbol» \s 14 c yeeo oiiaao aei
aoiia oinoi?o iaeei, aeaa oa o?e aaoa?ioeeee?/ieo caeeoee.

Iieacaia iiaeeea?noue ciyooy a?ae?aciiiiai caoenoo c io?eiaiiyi
aeueaeaa?aeii? a?oie aeey iiii- oa a?noinoi?eeueiaaieo iio?aeieo i??ieo,
oo?aio oa o?ioaio.

Ai?iaaoe?y ?iaioe. ?acoeueoaoe ?iaioe aeiiia?aeaeenue ia XIV
I?aeia?iaei?e eiioa?aioe?? c o?i?? oinoi?o (NOA, 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 oaiith aeena?oaoe?eii? ?iaioe iioae?eiaaii 4 noaoo?, a
yeeo iiai?noth a?aeia?aaeaii ci?no aeena?oaoe??.

No?oeoo?a oa ianya ?iaioe. Aeena?oaoe?eio ?iaioo aeeeaaeaii ia ….
noi??ieao, aiia neeaaea?oueny c anooio, /ioe?ueio /anoei, aeniiae?a,
nieneo oeeoiaaieo aeaea?ae c … iaeiaioaaiue oa aeiaeaoeo. ?iaioa ai?uo?
… oaaeeoeue. Ia?oa /anoeia aeena?oaoe?? ? iaeyaeii e?oa?aoo?e, yeee
i?enay/aii ?icaeyaeo iaoiae?a oinoi?eethaaiiy oo?aio, i??ieo oa o?ioaio
oa o?i?/ieo aeanoeainoae oinoi?eeueiaaieo iio?aeieo oeeo aaoa?ioeeee?a.
Aeani? aeine?aeaeaiiy aaoi?a aeeeaaeai? a ae?oa?e oa o?ao?e /anoeiao.

A ae?oa?e /anoei? ?icaeyioo? ?aaeoe?? i?yiiai oinoi?eethaaiiy
aaeiaai?aeaie o?eaaeaioiiai oinoi?o a?ae?acii?a oo?oo?ieo, 2-o??i?e oa
2-i??ie?eea?aaeueaeaa?ae?a, iieacaia iiaeeea?noue neioaco aeayeeo
aaoa?ioeeee?a ia iniia? io?eiaieo oinoi?iai?nieo iio?aeieo.

A o?ao?e /anoei? iienai? iaoiaee ciyooy a?ae?aciiiiai caoenoo c
io?eiaiiyi aeueaeaa?aeii? a?oie a oinoi?eeueiaaieo a?ae?aciiao.

*aoaa?oa /anoeia ai?uo? iaoiaeeee neioaco io?eiaieo niieoe. Eiie?aoiee
iniaenoee aianie aeena?oaioa. Aenia?eiaioaeueia /anoeia ?iaioe,
?ioa?i?aoaoe?y ?ic?aooie?a, aiae?c niaeo?aeueieo aeaieo oa anoaiiaeaiiy
aoaeiae neioaciaaieo niieoe aeeiiai? iniaenoi aeena?oaioii.

Iniiaiee ci?no ?iaioe

Iiiioinoi?eeueiaai? a?ae?aciie 2-oo?ee-, 2-(N-iaoeei??ie?e) oa
2-o??i?eea?aaeueaeaa?ae?a

Oinoi?eethaaiiy iacai?uaieo a?ae?acii?a

N-Oinoi?eeueiaai? iio?aei? ia?a?aoiaaieo aaoa?ioeeee?/ieo aeueaeaa?ae?a
iaiiaeeeai io?eiaoe ?aaeoe??th i?yiiai oinoi?eethaaiiy, oiio ui aiie
eaaei ?aaaothoue c aaeiaai?aeaie oinoi?o a ia?oo /a?ao ii ea?aii?euei?e
a?oi?. A ca SYMBOL 162 \f «Symbol» \s 14 c yceo c oeei iaie cae?eniaii
oinoi?eethaaiiy ?o aeeiaoeea?ae?acii?a. A?aeiii, ui a?ae?acii (1) a
?aaeoe?yo c aeaeo?io?eaie ((CF3CO)2O, PhSO2NCO, (CN)2C=C(CN)2) ooai?th?
i?iaeoeoe cai?uaiiy ye ii iieiaeaiith i SYMBOL 162 \f «Symbol» \s 14 c
youe aaoa?ioeeeeo, oae ? ii aecioeeee?/iiio aoiio aoaeaoeth
a?ae?aciiii? a?oie.

Anoaiiaeaii, ui oinoi?eethaaiiy a?ae?acii?a (1, 2) o?ea?ii?aeii oinoi?o
i?ioiaeeoue ?aa?inaeaeoeaii ii iieiaeaiith 5 aaoa?ioeeee?/ii? nenoaie c
ooai?aiiyi, a caeaaeiino? a?ae ni?aa?aeiioaiiy ?aaaaio?a, aeea?ii-
a?ii-, oa o?eaaoa?eeoino?i?a (3-8). Aeea?ii- oa a?iioino?ie ? oa?i?/ii
iano?eeeie niieoeaie ? oiio aoee ioa?aeoa?eciaai? i?ney ia?aoai?aiiy ?o
o a?aeiia?aei? ai?aee (9-12).

Anoaiiaeaii oaeiae, ui a?ae?aciiia a?oia a ?aaeoe?? i?yiiai
oinoi?eethaaiiy ? aeaeo?iiiaeiii?iei cai?nieeii, yeee cia/ii i?aeaeuo?
oaeaee?noue oinoi?eethaaiiy. Oae, yeui aeey oinoi?eethaaiiy oo?aio aai
o?ioaio o?ea?ii?aeii oinoi?o c ooai?aiiyi aeea?iioino?i?a, ca?aeii c
e?oa?aoo?ieie aeaieie, iio??aai ye ?ic/eiiee i??eaeei ? oaiia?aoo?a
aeecueei 100-120 0N, oi oinoi?eethaaiiy a?ae?acii?a (1, 2)
cae?enith?oueny a aaicie? iaa?oue i?e 5 0N.

O?enaaoa??eoino?ie oo?aio oa o?ioaio ooai?ththoueny eeoa i?e oaiia?aoo??
150-180 0N i?ioyaii 48 aiaeei, oiae? ye ooai?aiiy oino?io (7) i?e 20 0N
a i??eaeei? cae?i/o?oueny ca /ioe?e aiaeeie, a oino?io (8) — ca 48
aiaeei.

Aoaeiao niieoe (7-12) aeiaaaeaii niaeo?aie ssI? 1I, 13N, 31?, a o?i?/iee
neeaae — aeaiaioiei aiae?cii. I?enooi?noue a niaeo?ao II? neiaeaoo a
iaeano? 7.0-7.5 i./. i?aeoaa?aeaeo? iayai?noue aecioeeee?/iiai i?ioiia
a?ae?aciiii? a?oie. Neaiaee i?ioii?a oo?aiiaiai oeeeeo i?iyaeythoueny o
aeaeyae? aeaio aeoaeao?a a iaeano? 6.5-6.8 i./., a o?ioaiiaiai oeeeeo —
a iaeano? 7.1-7.5 i./., ui na?ae/eoue i?i i?ioiaeaeaiiy ?aaeoe?? ii
iieiaeaiith 5 aaoa?ioeeee?/ii? nenoaie.

Ia a?aei?io a?ae a?ae?acii?a (1, 2), iaea?eueo aeoeaiee a?ae?acii
2-(1-iaoee)i??ie?eea?aaeueaeaa?aeo ?aaao? c o?ea?ii?aeii oinoi?o
ianaeaeoeaii c ooai?aiiyi neeaaeii? noi?o? niieoe, aea ?aaeoe?y c iaio
aeoeaiei oinoi?eethth/ei aaaioii — aeeoai?ea?iioino?iii — i?ioiaeeoue
naeaeoeaii ii iieiaeaiith 5 oeeeeo c ooai?aiiyi oino?io (14), yeee
?aeaioeo?eiaaii ia?aoai?aiiyi a oino?iieneae 15.

Aoaeiao oino?iieneaeo (15) i?aeoaa?aeaeaii ssI? 1I oa 31? niaeo?aie.
Oae, iayai?noue aeaio aeoaeao?a c iaeiaeiaith eiinoaioith i?e 6.28 i./.
? 5.05 i./. oa neiaeao aecioeeee?/iiai (CH=N) i?ioiia i?e 7.26 i./.
na?ae/aoue i?i i?ioiaeaeaiiy ?aaeoe?? ii iieiaeaiith 5 aaoa?ioeeee?/ii?
nenoaie.

?c ae?ai?ae?a (9, 10) c aenieei aeoiaeii io?eiai? a?aeiia?aei? ieneaee
(16, 17), o?iieneaee (18,19) oa naeaiieneaee (20,21).

Niieoee (16-21) — ??aeeie aai oaa?ae? niieoee, aeia?a ?ic/eii? a
aaicie? oa oei?ioi?i?, noaa?euei? ia iia?o??. ?o aoaeiao aeiaaaeaii ssI?
31?, 13N, 1I niaeo?aie.

?aaeoe??th ai?aeioinoii?o?a (11,12) c n??eith c aenieeie aeoiaeaie
io?eiai? o?iieneaee (22, 23).

C oino?i?a (7, 8) c aenieei aeoiaeii aoee io?eiai? a?aeiia?aei? ieneaee
(24, 25), o?iieneaee (26, 27) oa naeaiieneaee (28, 29).

Aoaeiao niieoe (24-29) i?aeoaa?aeaeaii ssI? 31?, 13N, 1I niaeo?aie.

Oinoi?eethaaiiy 5-cai?uaieo a?ae?acii?a.

Aieea cai?niee?a o i SYMBOL 162 \f «Symbol» \s 14 c yoiio iieiaeaii?
aaoa?ioeeee?/ii? nenoaie ia ia?aa?a ?aaeoe?? oinoi?eethaaiiy aea/aii ia
iaea?eueo aeinooiieo iio?aeieo oo?oo?ieo.

Ciaeaeaii, ui a?ae?aciie 5-R oo?oo?ieo (30, 31) oinoi?eeththoueny
o?ea?ii?aeii oinoi?o ?aa?inaeaeoeaii a o?ao? iieiaeaiiy aaoa?ioeeee?/ii?
nenoaie c ooai?aiiyi aeea?iioino?i?a (32, 33), ye?, iiae?aii aei
io?eiaieo ?ai?oa aeea?iioino?i?a, oaeiae ? oa?i?/ii ianoaa?eueieie ?
oiio aoee ioa?aeoa?eciaai? i?ney ia?aoai?aiiy o a?aeiia?aei? ai?aee (34,
35).

A?ae?aciie (30) oa (31) nooo?ai aae??ciythoueny ca ?aaeoe?eiith
caeaoi?noth. Oae, yeui ?aaeoe?y a?ae?aciio oo?oo?ieo c o?ea?ii?aeii
oinoi?o a aaicie? i?ioiaeeoue ca aea? aiaeeie, oi ?aaeoe?y (31) ca oaeeo
aea oiia i?ioiaeeoue ca 20 ae?a eeoa ia 50 %. Ie??i oiai, a?ae?acii
(30), ia a?aei?io a?ae a?ae?aciio oo?oo?ieo, ?aaao? iaa?oue c oaeei
neaaeei oinoi?eethth/ei ?aaaaioii, ye aeeoai?eoei?oino?i, c ooai?aiiyi
oino?io (36).

Aoaeiaa io?eiaieo 3-oinoi?eeueiaaieo iio?aeieo i?aeoaa?aeaeaia II?
niaeo?aie. Oae, iayai?noue neiaeaoo i?e 7.5-8.0 i./. (CH=N) oa
iayaianoue neiaeaoo i?ioiio aaoa?ioeeee?/iiai e?eueoey i?e 5.72 i./.
na?ae/aoue i?i oa, ui oinoi?eethaaiiy i?ieoei ii o?aoueiio iieiaeaiith
aaoa?ioeeeeo.

?c ai?ae?a (34, 35) c aenieei aeoiaeii io?eiai? ?o ieneaee (37, 38) oa
o?iieneaee (39, 40).

Iayai?noue o i SYMBOL 162 \f «Symbol» \s 14 c yoiio iieiaeaii?
a?ae?aciio oo?oo?ieo ae?aoeeai?iia?oie — a?eueo neeueiiai
aeaeo?iiiaeiii?iiai cai?nieea a ii??aiyii? c a?ae?aciiiith a?oiith —
i?ecaiaeeoue aei a?eueoi? aeoeaaoe?? /aoaa?oiai iieiaeaiiy
aaoa?ioeeee?/ii? nenoaie, ia ui aeaco? a?eueo neeueiiiieueiee cnoa I4
(5.2 i./.) a ii??aiyii? c I3 (6.5 i./.). Iane?aeeii oeueiai ? oa, ui
a?ae?acii (41) aca?iiae?? ia o?eueee c o?ea?ii?aeii oinoi?o, aea ? c
iaio aeoeaiei oinoi?eethth/ei ?aaaaioii — o?eoei?eaeii oinoi?o – c
ooai?aiiyi aeeaaeiaaioino?i?a (42, 43) ( SYMBOL 100 \f «Symbol» \s 14
d ?=144 (Br) oa SYMBOL 100 \f «Symbol» \s 14 d ?=154 i./.
(Cl)), ye? ?aeaioeo?eiaai? ia?aoai?aiiyi a o?iai?ae (44).

Aoaeiao o?iai?aeo (44) aeiaaaeaii niaeo?ii II?: iayai?noue aeoaeaoo i?e
6.35 i./. oa a?aenooi?noue neaiaeo i?e 5.2 i./. na?ae/aoue i?i
i?ioiaeaeaiiy ?aaeoe?? ii /aoaa?oiio iieiaeaiith aaoa?ioeeee?/ii?
nenoaie.

Aeoaea oe?eaaei aeyaeany oie oaeo, ui oinoi?eethaaiiy a?ae?aciio (41)
a?eueo ia SYMBOL 162 \f «Symbol» \s 14 c ?iiei ?aaaaioii —
aeeoai?ea?iioino?iii — i?ioiaeeoue ii iieiaeaiith 3 aaoa?ioeeee?/ii?
nenoaie c ooai?aiiyi aeeoai?eoino?io (45), yeee ?aeaioeo?eiaaii
ia?aoai?aiiyi a o?iieneae (46).

Iayai?noue aeoaeaoo i?e 5.72 i./. oa a?aenooi?noue neaiaeo i?e 6.5 i./.
a niaeo?? II? o?iieneaeo (46) na?ae/aoue i?i i?ioiaeaeaiiy ?aaeoe?? ii
o?aoueiio iieiaeaiith aaoa?ioeeee?/ii? nenoaie.

1.3. 3,5-A?noinoi?eeueiaai? a?ae?aciie 2-oo?ee-,
2-(N-iaoeei??ie?e)-ea?aaeueaeaaeae?a.

Ciaeaeaii, ui io?eiai? ?ai?oa iiiioinoi?eeueiaai? a?ae?aciie anooiathoue
a ?aaeoe?th c o?ea?ii?aeii oinoi?o a a?eueo aei?noeeo oiiaao i?ae
aeo?aei? a?ae?aciie. Oae, niieoee (15, 16, 18) ?aaaothoue c o?ea?ii?aeii
oinoi?o a i??eaeei? c ooai?aiiyi aeea?iioino?i?a (47-49), ye?
?aeaioeo?eiaai? ia?aoai?aiiyi o a?aeiia?aei? o?iai?aee (50-52).

Eaae?noue oinoi?eethaaiiy cacia/aieo a?ae?acii?a ciaioo?oueny a ?yaeo
i??ie > oo?ai > o?ioai. Inoaii?e a ?aaeoe?th a?noinoi?eethaaiiy ia
anooia?. A iaeiaeiaeo oiiaao a?ae?acii (15) oinoi?eeth?oueny ca 10
aiaeei, a niieoee (16,18) — ca 48 aiaeei. Oe? ?acoeueoaoe
aeaiiino?othoue ??cieoeth a aeoeaiino? iiiioinoi?eeueiaaieo aeae?acii?a
ia iniia? oi?i?ei??ieo oa oo?oo?ieo.

Iai?yiie oinoi?eethaaiiy anoaiiaeaii i?e aea/aii? niaeo??a II?. Oae,
iayai?noue neiaeaoo aecioeeee?/iiai i?ioiio (CH=N) i?e 7.74 — 7.95 i./.
oa i?enooi?noue neaiaeo i?ioiio aaoa?ioeeee?/iiai e?eueoey i?e 6.84 —
7.19 i./. na?ae/aoue i?i i?ioiaeaeaiiy oinoi?eethaaiiy ii o?aoueiio
iieiaeaiith aaoa?ioeeee?/ii? nenoaie.

Aeyaeaia caeiiii??i?noue niinoa??aa?oueny ? aeey a?eueo neeaaeieo
noa-no?ao?a. Oae, o?iieneae (26) oinoi?eeth?oueny o?ea?ii?aeii oinoi?o
?aa?inaeaeoeaii ii o?aoueiio iieiaeaiith an?o aaoa?ioeeee?/ieo caeeoe?a
c ooai?aiiyi aeea?iioino?io (53), yeee ?aeaioeo?eiaaii ia?aoai?aiiyi o
a?aeiia?aeiee o?iai?ae (54).

sse ? o aeiaaeeo oino?i?a (50-52), a niaeo?? II? niieoee (54) ? aeoaeao
i?ioiio oo?aiiaiai oeeeeo i?e 7.27 i./. oa neiaeao CH=N- a?oie ( SYMBOL
100 \f «Symbol» \s 14 d = 7,8 i. /.), ui na?ae/eoue i?i i?ioiaeaeaiiy
?aaeoe?? ii o?aoueiio iieiaeaiith oo?aiiaiai oeeeeo.

Aeoeaaoe?y aeeiaoeea?ae?aciiiith a?oiith aaoa?ioeeee?/ieo nenoai
aeyaeeanue iano?eueee neeueiith, ui aaeaeiny cae?enieoe ?o i?yia
a?noinoi?eethaaiiy o?ea?ii?aeii oinoi?o a i??eaeei? c ooai?aiiyi
a?naeea?iioino?i?a (55, 56), ye? ?aeaioeo?eiaai? ia?aoai?aiiyi o
a?aeiia?aei? a?no?iai?aee (52, 57).

Aeoeai?noue a?ae?acii?a o oe?e ?aaeoe?? ia iaeiaeiaa ? caeaaeeoue a?ae
i?e?iaee aaoa?ioeeeeo. Oae, yeui o aeiaaeeo a?ae?aciio (13) ?aaeoe?y
i?ioiaeeoue ca 3 aeiae, oi aeey i?ioiaeaeaiiy ?aaeoe?? c a?ae?aciiii (1)
iio??aii aaea 14 ae?a. Aeey a?ae?aciio 2-o?ioaiiaiai aeueaeaa?aeo
?aaeoe?y cae?i/o?oueny ia noaae?? iiiioinoi?eeueiaaiiai iio?aeiiai.

I?enooi?noue aeaio aeaeo?iiiaeiii?ieo cai?niee?a o aaoa?ioeeee?
aeicaiey? eaaei (50N, 1 aeiaa) aaanoe a i?oi-iieiaeaiiy aea?
aeea?iioino?iia?oie c ooai?aiiyi a?naeea?iioino?io (58). A?i aoa
aeei?enoaiee aeey neioaco aeeaaoa?eeaeeoinoi??iaio (59), yeee aoei
?aeaioeo?eiaaii ia?aoai?aiiyi o a?no?iai?ae (60).

A?no?iai?ae (60) aoa oaeiae io?eiaiee cono??/iei neioacii.

I?e aeei?enoaii? a ?aaeoe?? i?yiiai oinoi?eethaaiiy oai?ea?ae?acii?a
aeueaeaa?ae?a ?aaeoe?y ?aea ii aoiio acioo c ooai?aiiyi aeea?iioino?i?a
(65, 66). O aeiaaeeo iaea?eueo aeoeaiiai aaoa?ioeeeeo — i??ieo i?ioean
ia cae?i/o?oueny ia ooai?aii? ae?a?iioino?io(62)- inoaii?e cacia?
aioo??oiueiiieaeoey?ii? oeeee?caoe?? c ooai?aiiyi ae?acaoinoi??iaiiai?
nenoaie (63). A?iioino?i ?aeaioeo?eiaaii ia?aoai?aiiyi a o?iai?ae (64).

Oaeei /eiii, io?eiai? iaie aeai? iieacothoue, ui aea??
aeeiaoeea?ae?acii?a aaoa?ioeeee?/ieo aeueaeaa?ae?a ye noano?ao?a aeey
oinoi?eethaaiiy aaoa?ioeeee?/ieo caeeoe?a ? aaeaeei ? aeicaiey? aaiaeeoe
iaeei oa aeaa aoiie oinoi?o a SYMBOL 112 \f «Symbol» \s 14 p
-iaaeeeoeia? aaoa?ioeeeee.

Iiii oa a?noinoi?eeueiaai? aeueaeaa?aee o?ioaio, oo?aio oa i??ieo

2.1. Iiiioinoi?eeueiaai? aeueaeaa?aee

A e?oa?aoo?? iienaii aeae?eueea iaoiae?a ia?aoai?aiiy a?ae?aciiii? a?oie
ia aeueaeaa?aeio. Aiie aacothoueny aieiaiei /eiii ia ieeniaii? aai
a?ae?ie?c? a?ae?aciiii? a?oie a neeueiieeneiio na?aaeiaeu?. Iaie aoa
ia?aiee iaoiae, a yeiio aeei?enoiaothoue iiia?aaeith aeoeaaoe?th C=N
ca SYMBOL 162 \f «Symbol» \s 14 c yceo a?ae?aciio aee?eoaaiiyi ai?iiiai
aoiia acioo. Ianooiiee eeneee a?ae?ie?c i?e oeueiio cae?enith?oueny a i
SYMBOL 162 \f «Symbol» \s 14 c yeeo oiiaao. Cai?iiiiiaaiee iaoiae
aeicaiey? i?iaiaeeoe i?ioean io?eiaiiy ea?aii?eueii? a?oie, iacaaaeath/e
ia aeia?a a?aeiio iecueeo no?ee?noue aeine?aeaeoaaieo aaoa?ioeeee?a a
eeneiio na?aaeiaeu?.

Aee?eoaaiiyi a?ae?acii?a (16-21) oa (24-29) iaoeeeiaeeaeii c ianooiiei
a?ae?ie?cii aiii?eieo nieae io?eiai? a?aeiia?aei? aeueaeaa?aee (68-75).

Cae?enieoe ?aaaia?aoe?th ea?aii?eueii? a?oie aaeaeiny ia a on?o
aeiaaeeao. Oae, ca aeaieie 31? niaeo??a iiaeia c?iaeoe aeniiaie, ui i?e
aee?eoaaii? aenieiioeeaio?eueieo naeaiieneae?a oino?i?a ooai?ththoueny
noi?o? i?iaeoeo?a ye N-, oae ? Se-aee?eoaaiiy, ye? ?icae?eeoe ia
aaeaeiny. A?ae?ie?c nieae, ui ooai?ththoueny c ai?ae?a (22, 23),
i?ioiaeeoue c ?ic?eaii N-? ca SYMBOL 162 \f «Symbol» \s 14 c yceo.

C oino?iieneaeo (15) i?e aee?eoaaii? oa ianooiiiio eeneiio a?ae?ie?c? c
aenieei aeoiaeii io?eiaii aeueaeaa?ae (76).

O aeiaaeeo 3-oinoi?eeueiaaieo a?ae?acii?a (39, 40) ciyooy a?ae?aciiiiai
caoenoo i?ioiaeeoue aeaaeei, aeueaeaa?aee (77, 78) ooai?ththoueny c
aenieeie aeoiaeaie.

A oie /an a?ae?ie?c a?aeiia?aeieo aiii?eieo nieae ai?ae?a (37, 38)
noi?iaiaeaeo?oueny ?ic?eaii N-? ca SYMBOL 162 \f «Symbol» \s 14 c yceo.

Aoaeiao iiiioinoi?eeueiaaieo aeueaeaa?ae?a aeiaaaeaii ssI? 1I, 31?, 13N
niaeo?aie. Iayai?noue a II? niaeo?ao neiaeaoo a iaeano? 9.2-9.5 i./. oa
a?aenooi?noue neiaeao?a i?e 7.0-8.0 i./. (CH=N), oa i?e 3.0-3.5 i./.
(NMe2) na?ae/aoue i?i ooai?aiiy oi?i?e iio?aeieo oinoi?eeueiaaieo
aaoa?ioeeee?a.

2.2. A?noinoi?eeueiaai? aeueaeaa?aee

Ciyooy a?ae?aciiiiai caoenoo o aeiaaeeo a?noinoi?eeueiaaieo a?ae?acii?a
(50-52, 57) i?ioiaeeoue ia iano?eueee iaeiicia/ii, ye aeey ?o
iiiioinoi?eeueiaaieo aiaeia?a. Oae, ciyooy a?ae?aciiii? caoenii? a?oie
aoei oni?oiei eeoa o aeiaaeeo iio?aeieo oo?oo?ieo.

Aeueaeaa?ae (80) iiaea aooe io?eiaiee eeoa a ?ia?oi?e aoiinoa??. A
i?enooiino? eenith iia?o?y i?e eeneioiiio a?ae?ie?c? a?aeiia?aeii? nie?
aoa io?eiaiee a?no?iai?ae i??ineecaai? eeneioe (81).

A niaeo?? II? eeneioe (81) a?aenooi?e neaiae i?ioiia i?e 9.2 i./.
(NI=I), a a ?* niaeo?? ? nioae SYMBOL 110 \f «Symbol» \s 14 n NI 1700
ni-1 oa SYMBOL 110 \f «Symbol» \s 14 n II 3600 ni-1, ui na?ae/eoue i?i
ieeniaiiy aeueaeaa?aeo a eeneioo.

Aee?eoaaiiy oa ianooiiee eeneioiee a?ae?ie?c a?noinoi?eeueiaaieo
a?ae?acii?a 2-(N-iaoeei??ie?e)ea?aaeueaeaa?aeo (50-57) i?ecaiaeeoue aei
ooai?aiiy i?o?ee?a (82,83) cai?noue i/?eoaaieo aeueaeaa?ae?a.

A niaeo?ao II? i?o?ee?a (82, 83) a?aenooi?e neaiae i?ioiia i?e 9.2 i./.
(NI=I), a a ?* niaeo?? ? nioaa iiaeeiaiiy SYMBOL 110 \f «Symbol» \s 14
n CN 2250 ni-1.

Iiii- oa a?noinoi?eeueiaai? oi?i?eiio?aei? neioaciaaieo aaoa?ioeeee?a c
ai?iaie eaaei ooai?ththoue a?aeiia?aei? aciiaoeie (84,85), ui ?
aeaiiino?aoe??th ?o neioaoe/ieo iiaeeeainoae.

AENIIAEE

Anoaiiaeaii, ui aca?iiae?y N,N-aeeiaoeea?ae?acii?a oo?oo?ieo, 2-o??i?e-
oa 2-(1-iaoee)i??ie?eea?aaeueaeaa?ae?a c o?ea?ii?aeii oinoi?o
i?ioiaeeoue ?aa?inaeaeoeaii ii i SYMBOL 162 \f «Symbol» \s 14 c yoiio
iieiaeaiith aaoa?ioeeeeo.

Iieacaii, ui i?e iayaiino? a i SYMBOL 162 \f «Symbol» \s 14 c yoiio
iieiaeaii? aaoa?ioeeeeo aeoeaioi?ieo oa neaaiaeiii?ieo cai?niee?a
oinoi?eethaaiiy i?ioiaeeoue ?aa?inaeaeoeaii ii o?aoueiio iieiaeaiith
oeeeeo, oiae? ye ae?aoeeai?iia?oia ni?yiiao? oinoi?eethaaiiy a /aoaa?oa
iieiaeaiiy.

Anoaiiaeaii, ui ?aa?inaeaeoeai?noue oinoi?eethaaiiy caeaaeeoue ye a?ae
aeaeo?iiieo aoaeo?a, oae oaeiae ? a?ae noa?e/ieo aoaeo?a oinoi?eethth/eo
?aaaaio?a.

A?ae?aciiia a?oia, ye aeaeo?iiiaeiii?iee cai?niee, nooo?ai i?enei?th?
?aaeoe?th oinoi?eethaaiiy, ui aeicaiey? a i SYMBOL 162 \f «Symbol» \s 14
c yeeo oiiaao aaiaeeoe aei aoiia oinoi?o iaeei, aeaa ? o?e
aaoa?ioeeee?/ieo caeeoee, a oaeiae aaanoe aeaa oinoi?iai?nieo cai?nieee
a aaoa?ioeeee.

?ic?iaeaii niin?a ci?ooy a?ae?aciiiiai caoenoo a aeine?aeaeoaaieo
nenoaiao: aee?eoaaiiy oa ianooiiee a?ae?ie?c, ui aeicaieeei io?eiaoe
oe?eee ?yae iiii- oa a?noinoi?eeueiaaieo aeueaeaaeae?a i??ieo, oo?aio oa
o?ioaio.

Ciaeaeaii, ui i?e ciyoo? caoenii? a?oie a a?ae?aciiao
a?noinoi?eeueiaaieo i??ie?a ooai?ththoueny i??ie?ei?o?eee.

A i?aeoeeo i?aai?/ii? o?i?? oinoi?o aaaaeai? a?ae?aciie oo?oo?ieo,
2-o??i?e- oa 2-i??ie?eea?aaeueaeaa?ae?a ye eeth/ia? niieoee aeey
i?aia?aoeaiiai neioaco a?aeiia?aeieo oinoi?eeueiaaieo aaoa?ioeeee?a.

Iniiaiee ci?no aeena?oaoe?? aeeeaaeaiee a oaeeo ioae?eaoe?yo:

Tolmachev A.A., ivonin S.P., Anishchenko A.A., Pinchuk A.M.

5-Phosphorylated Furfural and Thiophenecarboxaldehyde Derivatives.
//

Heteroatom Chemistry. — 1998. – Vil. 9, ? 5. — ?. 461-470.

Ivonin S.P., Anishchenko A.A., Kurochkin A.F., and Tolmachev A.A.

Phosphorylation of 5-Substituted Furfurals. // Hetroatom
Chemistry. — 1998. – Vol. 9, ? 6. — P. 559-563.

Eo?i/eei A.O., Oieia/aa A.A., Eaiiei N.I., Aieuaiei A.A.

N,N-Aeeiaoeeaeae?aciiu oo?oo?iea, oinoi?eee?iaaiiua a iiei-

aeaiea 3. // AEo?i. iau. oeiee — 1998.- O. 68., Aui. 4.- N.
701-702.

Eaiiei N.I., Aieuaiei A.A., Eo?i/eei A.O., Oieia/aa A.A.,

Na?aethe A.I. 3-Oinoi?eee?iaaiiua N,N-aeeiaoeeaeae?aciiu oo?oo-

?iea. // A?niee AeAeO.- 1998 — ? 3 — N. 125-126.

Ivonin S.P., Anishnhenko A.A., Terikovskaya T.E., Tolmachev A.A.

C-Phosphorylated derivatives of 2-thiophenecarboxaldehyde, furfural
and

1-methyl-2-pyrrolecarboxaldehyde // XIV International Conference
on

Phosphorus Chemistry (Cincinnati, Ohio, USA, July 12-17, 1998):
Abstr. —

271.

?aii?i N.I., Ai?uaiei A.I., Eo?i/e?i I.O., Oa?eeianueea O.?.,

Oieia/aa A.I. N-oinoi?eeueiaai? iio?aei? 2-o?ai?eea?aaeueaeaa?aeo,

oo?oo?ieo oa 1-iaoee-2-i??ie?eea?aaeueaeaa?aeo. // XVIII
Oe?a?inueea

eiioa?aioe?y c i?aai?/ii? o?i?? (Aei?i?iiao?ianuee, 6-9 aeiao. 1998
?.):

Oac. aeii. – Aei?i?iiao?ianuee, AeAeO, 1998. -n. 50.

AIIIOAOeEss

Aieuaiei A.A. N-oinoi?eee?iaaiiua i?iecaiaeiua oo?oo?iea, 2-oeaiee- e
2-(N-iaoeeie??ieee) ea?aaeueaeaaeaeia

Aeenna?oaoeey ia nieneaiea o/aiie noaiaie eaiaeeaeaoa oeie/aneeo iaoe ii
niaoeeaeueiinoe 02.00.03.- i?aaie/aneay oeiey.- Aeiai?iiao?ianeee
ainoaea?noaaiiue oieaa?neoao, Aeiai?iiao?iane, 1999. Caueuaaony 4
iao/iuo ?aaiou, iinayuaiiua neioaco iiii- e aen- oinoi?eee?iaaiiuo
aeueaeaaeaeia (-ecauoi/iuo a?iiaoe/aneeo aaoa?ioeeeeia n eniieueciaaieai
N,N-aeeiaoeeaeae?aciiiie caueou aeey aeueaeaaeaeiie ooieoeee e eco/aieth
aeeyiey N,N-aeeiaoeeaeae?aciiiie a?oiiu ia ?aaeoeeth i?yiiai
oinoi?eee?iaaiey (-ecauoi/iuo aaoa?ioeeeeia. Iieacaii, /oi
oinoi?eee?iaaiea N,N-aeeiaoeeaeae?aciiia oo?oo?iea e
2-oeaieeaeueaeaaeaea o?aoa?iienoui oinoi?ii i?ienoiaeeo ?aaeinaeaeoeaii
ii iyoiio iieiaeaieth aaoa?ioeeeee/aneie nenoaiu e, a caaeneiinoe io
niioiioaiey ?aaaaioia e oneiaee i?ioaeaiey ?aaeoeee, i?eaiaeeo e
ia?aciaaieth aeea?ii-, a?ii- e o?aoe/iuo oinoeiia. Aeea?ii- e
a?iioinoeiu aaeaeo ianoaaeeueiinoe auee ioa?aeoa?eciaaiu i?aa?auaieai a
niioaaonoaothuea aieaeu. Iaeaieaa aeoeaiue aeae?acii
2-(1-iaoee)-ie??ieeeea?aaeueaeaaeaea a yoie ?aaeoeee ?aaae?oao
ianaeaeoeaii, aai naeaeoeaiia oinoi?eee?iaaiea oaeaeinue inouanoaeoue
aeeoaieea?iioinoeiii. Ec aieaeia, aeeaieaeia e oinoeiia iieo/aiu
niioaaonoaothuea ieene, oeiieene e naeaiieene.

Iieacaii, /oi aeae?aciiu 5-R-oo?oo?iea ( R= Me, i-BrPh, P(O)(NR2) 2,
P(S)(NR2) 2) oinoi?eee?othony o?aoa?iienoui oinoi?ii ?aaeinaeaeoeaii ii
o?aoueaio iieiaeaieth aaoa?ioeeeee/aneie nenoaiu n ia?aciaaieai
niioaaonoaothueo aeea?iioinoeiia, eioi?ua oaeaea auee ieeneaiu aei
niioaaonoaothueo P(V) i?iecaiaeiuo. ?aaeinaeaeoeaiinoue iineaaeothuaai
oinoi?eee?iaaiey oaeaea caaeneo io noa?e/aneeo yooaeoia ?aaaaioia.
Ioia/aaony iiieaeaiiay ?aaeoeeiiiay niiniaiinoue yae?a oeioaia a
?aaeoeee i?yiiai oinoi?eee?iaaiey, aneaaenoaea /aai oaeaaony
inouanoaeoue oieueei iiiioinoi?eee?iaaiea.

Iieacaia aiciiaeiinoue niyoey aeae?aciiiie caueou /a?ac aeeeee?iaaiea
iieo/aiiuo iiiioinoi?eee?iaaiiuo aeae?aciiia n iineaaeothuei eeneioiui
aeae?ieecii. I?e niyoee aeae?aciiiie caueou o aenoeiaieaeiiai
i?iecaiaeiiai iieo/aii i?iecaiaeiia ie?ineecaaie eeneiou. Niyoea
aeae?aciiiie caueou o aenoinoi?eee?iaaiiuo i?iecaiaeiuo
2(1-iaoee)-ie??ieeeea?aaeueaeaaeaea i?eaiaeeo e ia?aciaaieth
niioaaonoaothueo ieo?eeia.

Eeth/aaua neiaa: N,N-aeeiaoeeaeae?aciiiay caueoa, oinoi?eee?iaaiea,
(-ecauoi/iua aaoa?ioeeeeu, aeea?iioinoeiu, a?iioinoeiu, o?aoe/iua
oinoeiu, ?aaeinaeaeoeaiinoue, aeueaeaaeaeu.

AIIOAOe?ss

Ai?uaiea A.I. N-oinoi?eeueiaai? iio?aei? 2-oo?ee, 2-o??i?e- oa
2-(N-iaoeeie?ie?e) ea?aaeueaeaaeae?a

Aeena?oaoe?y ia caeiaoooy iaoeiaiai nooiaiy eaiaeeaeaoa o?i?/ieo iaoe ca
oaoii 02.00.03.-i?aai?/ia o?i?y.- Aei??iiao?ianueeee aea?aeaaiee
oi?aa?neoao, Aei?i?iiao?ianuee, 1999. Caoeuathoueny /ioe?e iaoeiaeo
i?aoe?, ye? i?enay/ai? neioaco iiii- oa a?n- oinoi?eeueiaaieo
aeueaeaa?ae?a (-caaaa/aieo a?iiaoe/ieo aaoa?ioeeee?a c aeei?enoaiiyi
N,N-aeeiaoeea?ae?aciiiiai caoenoo aeey aeueaeaa?aeii? ooieoe?? oa
aea/aiith aieeao N,N-aeeiaoeea?ae?aciiii? a?oie ia ?aaeoe?th i?yiiai
oinoi?eethaaiiy (-iaaeeeoeiaeo aaoa?ioeeee?a. Iieacaii, ui
oinoi?eethaaiiy N,N-aeeiaoeea?ae?acii?a oo?oo?ieo oa 2-
o??i?eaeueaeaa?aeo o?ea?ii?aeii oinoi?o i?ioiaeeoue ?aa?inaeaeoeaii ii
i(yoiio iieiaeaiith aaoa?ioeeee?/ii? nenoaie ?, a caeaaeiino? a?ae
ni?aa?aeiioaiiy ?aaaaio?a oa oiia i?iaaaeaiiy ?aaeoe?e i?ecaiaeeoue aei
ooai?aiiy ae?a?ii-, a?ii- oa o?aoeiieo oino?i?a. Ae?a?ii oa a?iioino?ie
aeyaeeenue iano?eeeie ? oiio aoee ioa?aeoa??ciaai? ia?aoai?aiiyi o
a?aeiia?aei? ai?aee. Iaea?eueo aeoeaiee a?ae?acii
2-(1-iaoee)-i??ie?eea?aaeueaeaa?aeo a oe?e ?aaeoe?? ?aaao? ianaeaeoeaii,
eiai naeaeoeaia oinoi?eethaaiiy aaeaeiny cae?enieoe
aeeoai?ea?iioino?iii. Ai?aee, ae?ai?aee oa oino?ie aoee ieeniai? aei
a?aeiia?aeieo ieneae?a, o?iieneae?a oa naeaiieneae?a.

Iieacaii, ui a?ae?aciie 5-R-oo?oo?ieo ( R= Me, i-BrPh, P(O)(NR2)2,
P(S)(NR2)2) oinoi?eeththoueny o?ea?ii?aeii oinoi?o oaeiae
?aa?inaeaeoeaii ii o?aoueiio iieiaeaiith aaoa?ioeeee?/ii? nenoaie c
ooai?aiiyi a?aeiia?aeieo aeea?iioino?i?a, ye? oaeiae aoee ieeniai? aei
a?aeiia?aeieo P(V) iio?aeieo. ?aa?inaeaeoeai?noue iiaoi?iiai
oinoi?eethaaiiy caeaaeeoue a?ae noa?e/ieo ?oaeo?a ?aaaaio?a.
A?aei?/a?oueny cieaeaia ?aaeoe?eia caeaoi?noue yae?a o?ioaio a ?aaeoe??
i?yiiai oinoi?eethaaiiy oa iaiiaeeea?noue eiai iiaoi?iiai
oinoi?eethaaiiy. C aeayeeo a?noinoi?eeueiaaieo iio?aeieo oo?oo?ieo oa
2(1-iaoeeie?ie?e)ea?aaeueaeaa?aeo io?eiai? aaoa?oeeee?/i? iio?aei?.

Iieacaii iiaeeea?noue ciyooy a?ae?aciiiiai caoenoo /a?ac aee?eoaaiiy
io?eiaieo iiiioinoi?eeueiaaieo a?ae?acii?a c ianooiei eeneioiei
a?ae?ie?cii. Ciyooy a?ae?aciiiiai caoenoo o aeiaaeeo a?noinoi?eeueiaaieo
iio?aeieo ia caaaeaee i?ecaiaeeoue aei a?aeiia?aeieo aeueaeaa?ae?a. A
?ac? a?no?iai?aeiiai iio?aeiiai io?eiaii iio?aeia i??ineecaai? eeneioe.
I?e ciyoo? aeae?aciiiiai caoenoo o a?noinoi?eeueiaaieo iio?aeieo
2(1-iaoee)-i??ieaeth aoee aeaeaeai? a?aeiia?aei? i?o??ee.

Eeth/ia? neiaa: N,N-aeeiaoeea?ae?aciiiee caoeno, oinoi?eethaaiiy,
(-iaaeeeoeia? aaoa?ioeeeee, ae?a?iioino?ie, a?iioino?ie, o?aoeii?
oino?i?e, ?aa?inaeaeoeai?noue, aeueaeaa?aee.

ANNOTATION

Anishchenko A.A. C-Phosphorylated derivatives of furfural, 2-
thiophencarboxaldehyde and 1-methyl-2-pyrrolecarboxaldehyde.

The dissertation for chemical sciences candidate degree on 02.00.03 —
organic chemistry speciality taking,- Dnipropetrovsk State university,
Dnipropetrovsk, 1999. 4 scientific works devoted to mono- and bis-
phosphorylated aldehydes synthesis of electron-rich aromatic
heterocycles with N,N-dimethylhydrazone protection for aldehyde function
and influence of N,N-dimethylhydrazone group on direct phosphorylation
electron-rich heterocycles are defended. All is shown, that
phosphorylation of N,N-dimethylhydrazones of furfural and 2-
thiophenecarboxaldehyde by phosphorus tribromide proceeds
regioselectively on fifth position of heterocyclic system and in
dependance on correlation of reagents and reaction conditions leads to
formation of dibrom-, brom- and tertiary phosphines. Because of their
unstability dibrom- and bromphosphines were characterized by convertion
in corresponding amides more active hydrazones of of
1-methyl-2-pyrrolecarboxaldehyde reacts not selectively in this
reaction. Its regioselective phosphorylation succesfuly realised by
dephenylebromphosphine. The corresponding oxides, tiooxides and
selenooxides have got from amides derivative P(III) and phosphines.

It was shown, that 5-R-furfural hydrazones ( R= Me, i-BrPh, P(O)(NR2)2,
P(S)(NR2)2)are phosphorylated regioselectively by phosphorus tribromide
on third position of heterocycle system with forming of corresponding
dibromphosphines, that also were oxidated to corresponding P(V)
derivatives. Regioselectivity of the second phosphorylation depends on
steric effects of reagents too. It is noted decreasing reactive ability
of thiophene nucleus in reaction of direct phosphorylation, leading to
monophosphorylation only.

It is shown the possibility of cancelling of hydrazone protection
through alkilation of obtained monophosphorylated hydrazones with the
following acidic hydrolysis. During the cancelling of hydrazone
protection from bistioamide derivative furoic acide derivative was
obtained.

Cancelling of hydrazone protection from bisphosphorylated derivatives of
1-methyl-2-pyrrolecarboxaldehyde leads to formation of corresponding
nitriles.

Key words: N,N-dimethylhydrazone protection, phosphorylation,
electron-rich aromatic heterocycles, dibromphosphines, bromphosphines,
tertiary phosphines, regioselectivity, aldehydes.

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