POLAR EFFECTS IN FREE-RADICAL REACTIONS - HOMOLYTIC HETEROAROMATIC SUBSTITUTIONS BY ALKYL BROMIDES

被引：39

作者：

MINISCI, F

FONTANA, F

PIANESE, G

YAN, YM

机构：

[1] Dipartimento di Chimica del Politecnico, 20133 Milano

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 16期

关键词：

D O I：

10.1021/jo00068a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkyl bromides have been utilized for the first time as radical sources for heteroaromatic substitution. A variety of Procedures was revealed to be successful for bromine abstraction: Bu3SnH with AIBN, (Me3Si)3SiH with AIBN, PhSiH, Ph2SiH2, or Et3SiH associated with peroxides (H2O2, t-BuOOH, (t-BuO)2, (t-BuOOCO)2, (PhCOO)2). The importance of the polar effects is discussed.

引用

页码：4207 / 4211

页数：5

共 17 条

[1] BERANEK I, 1989, NATO ADV SCI I C-MAT, V260, P303
[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] RATE CONSTANTS AND ARRHENIUS PARAMETERS FOR THE REACTIONS OF PRIMARY, SECONDARY, AND TERTIARY ALKYL RADICALS WITH TRI-NORMAL-BUTYLTIN HYDRIDE
CHATGILIALOGLU, C
INGOLD, KU
SCAIANO, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (26) : 7739 - 7742
[4] ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS IN SYNTHESIS
CHATGILIALOGLU, C
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (04) : 188 - 194
[5] ABSOLUTE RATE CONSTANTS FOR THE REACTION OF TRIETHYLSILYL RADICALS WITH ORGANIC HALIDES
CHATGILIALOGLU, C
INGOLD, KU
SCAIANO, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (19) : 5123 - 5127
[6] 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
[7] 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
[8] 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
[9] 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
[10] REDUCTION OF SILICON-HYDROGEN BOND STRENGTHS
KANABUSKAMINSKA, JM
HAWARI, JA
GRILLER, D
CHATGILIALOGLU, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (17) : 5267 - 5268

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