A NOVEL SUBSTITUTION-REACTION BY PHOTOINDUCED ELECTRON-TRANSFER BETWEEN PYRIDINE-DERIVATIVES AND ALKYLTIN COMPOUNDS

被引：14

作者：

MINISCI, F

FONTANA, F

CARONNA, T

ZHAO, L

机构：

[1] Dipartimento di Chimica del Politecnico, 20133 Milano

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 22期

关键词：

D O I：

10.1016/S0040-4039(00)79851-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photolysis of pyridine derivatives in the presence of SnBU4 or Sn2Bu6 leads to butyl derivatives in the alpha and gamma positions. With 2,4-dicyanopyridine ipso-substitution of the cyano groups with the butyl groups exclusively occurs. With 4-cyanopyridine both ipso-substitution and substitution at the 2-position take place. A photo-induced electron-transfer mechanism is suggested.

引用

页码：3201 / 3204

页数：4

共 14 条

[1] BACIOCCHI E, COMMUNICATION
[2] A NEW GENERAL-METHOD OF HOMOLYTIC ALKYLATION OF PROTONATED HETEROAROMATIC BASES
CASTALDI, G
MINISCI, F
TORTELLI, V
VISMARA, E
[J]. TETRAHEDRON LETTERS, 1984, 25 (35) : 3897 - 3900
[3] FREE-RADICAL DIAZO COUPLING - A NEW GENERAL REACTION OF DIAZONIUM SALTS
CITTERIO, A
MINISCI, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (09) : 1759 - 1761
[4] HOMOLYTIC ALKYLATION OF NAPHTHOQUINONE AND METHYL-NAPHTHOQUINONE - ENTHALPIC, STERIC AND POLAR EFFECTS
COPPA, F
FONTANA, F
MINISCI, F
BARBOSA, MCN
VISMARA, E
[J]. TETRAHEDRON, 1991, 47 (35) : 7343 - 7352
[5] NEW GENERAL PROCESSES OF HOMOLYTIC ALKYLATION OF HETEROAROMATIC BASES BY T-BUOOH OR (T-BUO)2 AND ALKYLIODIDES
FONTANA, F
MINISCI, F
BARBOSA, MCN
VISMARA, E
[J]. ACTA CHEMICA SCANDINAVICA, 1989, 43 (10): : 995 - 999
[6] HOMOLYTIC ALKYLATION OF HETEROAROMATIC BASES - THE PROBLEM OF MONOALKYLATION
FONTANA, F
MINISCI, F
BARBOSA, MCN
VISMARA, E
[J]. TETRAHEDRON, 1990, 46 (07) : 2525 - 2538
[7] NEW GENERAL AND CONVENIENT SOURCES OF ALKYL RADICALS, USEFUL FOR SELECTIVE SYNTHESES
FONTANA, F
MINISCI, F
VISMARA, E
[J]. TETRAHEDRON LETTERS, 1988, 29 (16) : 1975 - 1978
[8] SUBSTITUTIONS BY NUCLEOPHILIC FREE-RADICALS - A NEW GENERAL REACTION OF HETEROAROMATIC BASES
MINISCI, F
FONTANA, F
VISMARA, E
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (01) : 79 - 96
[9] POLAR EFFECTS IN FREE-RADICAL REACTIONS - RATE CONSTANTS IN PHENYLATION AND NEW METHODS OF SELECTIVE ALKYLATION OF HETEROAROMATIC BASES
MINISCI, F
VISMARA, E
FONTANA, F
MORINI, G
SERRAVALLE, M
GIORDANO, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (23) : 4411 - 4416
[10] HOMOLYTIC ALKYLATION OF PROTONATED HETEROAROMATIC BASES BY ALKYL IODIDES, HYDROGEN-PEROXIDE, AND DIMETHYL-SULFOXIDE
MINISCI, F
VISMARA, E
FONTANA, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) : 5224 - 5227

← 1 2 →