Radical Intermediates in Reactions of Mixed Phosphonium-Iodonium Ylides

被引：6

作者：

Nekipelova, T. D. ^{[1
]}

Motyakin, M. V. ^{[1
,2
]}

Kasparov, V. V. ^{[1
]}

Degtyarev, E. N. ^{[1
,2
]}

Levina, I. I. ^{[1
]}

Potapov, I. D. ^{[1
,3
]}

Podrugina, T. A. ^{[3
]}

机构：

[1] Russian Acad Sci, Emanuel Inst Biochem Phys, Moscow 119334, Russia

[2] Russian Acad Sci, Semenov Fed Sci Ctr Phys Chem, Moscow 119991, Russia

[3] Lomonosov Moscow State Univ, Moscow 119992, Russia

来源：

RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY B | 2019年 / 13卷 / 06期

关键词：

phosphonium-iodonium ylides; photolysis; reaction with acetylenes; radical intermediates; EPR; P-31; NMR; NUCLEOPHILIC-SUBSTITUTION;

D O I：

10.1134/S1990793119060265

中图分类号：

O64 [物理化学（理论化学）、化学物理学]; O56 [分子物理学、原子物理学];

学科分类号：

070203 ; 070304 ; 081704 ; 1406 ;

摘要：

The active intermediates generated in the photolysis of phosphonium-iodonium ylides and their reaction with acetylenes have been studied with electron and nuclear magnetic resonance spectroscopy. The radical mechanism of the ylides decomposition and of the interaction with acetylenes has been established using a stable nitroxyl radical. The radical products of these reactions have been monitored for the first time by EPR, and their spectroscopic parameters were determined. The chemical structure of the active intermediates of the reactions under study has been proposed.

引用

页码：907 / 914

页数：8

共 20 条

[1] BUCK HM, 1970, RECL TRAV CHIM PAY-B, V89, P1085
[2] PHOTOCHEMISTRY OF DIARYLIODONIUM SALTS
DEKTAR, JL
HACKER, NP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) : 639 - 647
[3] Poly(3-Hydroxybutyrate) Matrices Modified with Iron(III) Complexes with Tetraphenylporphyrin. Analysis of the Structural Dynamic Parameters
Karpova, S. G.
Olkhov, A. A.
Bakirov, A. V.
Chvalun, S. N.
Shilkina, N. G.
Popov, A. A.
[J]. RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY B, 2018, 12 (01) : 142 - 154
[4] Levin Y.A., 1978, HOMOLYTIC CHEM PHOSP
[5] Dichloromethane as solvent and reagent: a case study of photoinduced reactions in mixed phosphonium-iodonium ylide
Levina, Irina I.
Klimovich, Olga N.
Vinogradov, Dmitrii S.
Podrugina, Tatyana A.
Bormotov, Denis S.
Kononikhin, Alexey S.
Dement'eva, Olga V.
Senchikhin, Ivan N.
Nikolaev, Evgeny N.
Kuzmin, Vladimir A.
Nekipelova, Tatiana D.
[J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2018, 31 (07)
[6] UNSTABLE INTERMEDIATES .110. HYPERCONJUGATION BY GROUPS CONTAINING HEAVY ATOMS - ELECTRON-SPIN RESONANCE STUDIES OF CARBON RADICALS HAVING BETA-SNR3,BETA-PR2,BETA-PR+3,BETA-ASR2,BETA-ASR+3 AND BETA-ASO3H GROUPS
LYONS, AR
SYMONS, MCR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS II, 1972, 68 (04): : 622 - &
[7] Phosphonium-iodonim ylides in nucleophilic substitution reactions
Matveeva, E. D.
Podrugina, T. A.
Grishin, Yu. K.
Pavlova, A. S.
Zefirov, N. S.
[J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (02) : 201 - 206
[8] Initiated pseudo-[3+2] cycloaddition of mixed phosphonium-iodonium ylides to acetonitrile
Matveeva, E. D.
Podrugina, T. A.
Pavlova, A. S.
Mironov, A. V.
Zefirov, N. S.
[J]. RUSSIAN CHEMICAL BULLETIN, 2008, 57 (10) : 2237 - 2239
[9] One-pot process in phosphonium-iodonium ylides: nucleophilic substitution and the Wittig reaction
Matveeva, E. D.
Podrugina, T. A.
Pavlova, A. S.
Mironov, A. V.
Zefirov, N. S.
[J]. RUSSIAN CHEMICAL BULLETIN, 2008, 57 (02) : 400 - 405
[10] Synthesis and structure of mixed phosphonium-iodonium ylide
Matveeva, ED
Podrugina, TA
Grishin, YK
Tkachev, VV
Zhdankin, VV
Aldoshin, SM
Zefirov, NS
[J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 39 (04) : 536 - 541

← 1 2 →