On the mechanism of the intramolecular samarium Barbier reaction. Probes for formation of radical and organosamarium intermediates

被引：67

作者：

Curran, DP

Gu, X

Zhang, W

Dowd, P

机构：

[1] Department of Chemistry, University of Pittsburgh, Pittsburgh

来源：

TETRAHEDRON | 1997年 / 53卷 / 27期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4020(97)00608-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new type of mechanistic probe for the intramolecular samarium Barbier reaction has been designed, and two different probe substrates have been investigated in detail. Remarkably, no unambiguous evidence could be obtained in favor of any of the obvious intermediates (free alkyl or alkoxy radicals, ketyls, organosamarium species) that are postulated for this reaction. Several possibilities for modified mechanisms are suggested. (C) 1997 Elsevier Science Ltd.

引用

页码：9023 / 9042

页数：20

共 48 条

[11] Lewis acids in diastereoselective processes involving acyclic radicals
Guindon, Y
Guerin, B
Rancourt, J
Chabot, C
Mackintosh, N
Ogilvie, WW
[J]. PURE AND APPLIED CHEMISTRY, 1996, 68 (01) : 89 - 96
[12] RATE CONSTANTS FOR THE REACTIONS OF PRIMARY ALKYL RADICALS WITH SMI2 IN THF/HMPA
HASEGAWA, E
CURRAN, DP
[J]. TETRAHEDRON LETTERS, 1993, 34 (11) : 1717 - 1720
[13] ADDITIVE AND SOLVENT EFFECTS ON SMI2 REDUCTIONS - THE EFFECTS OF WATER AND DMPU
HASEGAWA, E
CURRAN, DP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) : 5008 - 5010
[14] ALKYLATION OF DIANIONS OF BETA-KETO-ESTERS
HUCKIN, SN
WEILER, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) : 1082 - 1087
[15] THE REACTION OF SAMARIUM(III) IODIDE WITH SAMARIUM METAL IN TETRAHYDROFURAN - A NEW METHOD FOR THE PREPARATION OF SAMARIUM(II) IODIDE
IMAMOTO, T
ONO, M
[J]. CHEMISTRY LETTERS, 1987, (03) : 501 - 502
[16] A MILD AND CONVENIENT METHOD FOR THE REDUCTION OF ORGANIC HALIDES BY USING A SMI2-THF SOLUTION IN THE PRESENCE OF HEXAMETHYLPHOSPHORIC TRIAMIDE (HMPA)
INANAGA, J
ISHIKAWA, M
YAMAGUCHI, M
[J]. CHEMISTRY LETTERS, 1987, (07) : 1485 - 1486
[17] Jorgenson MJ., 1970, ORG REACTIONS, V18, P1
[18] KABAN HB, 1981, TETRAHEDRON S1, V37, P1175
[19] KAGAN HB, 1990, NEW J CHEM, V14, P453
[20] NOVEL REDUCTION OF CARBOXYLIC-ACIDS, ESTERS, AMIDES AND NITRILES USING SAMARIUM DIIODIDE IN THE PRESENCE OF WATER
KAMOCHI, Y
KUDO, T
[J]. CHEMISTRY LETTERS, 1993, (09) : 1495 - 1498

← 1 2 3 4 5 →