Formation of cyclopropanes by holmolytic substitution reactions of 3-iodopropyl radicals: Preparative and rate studies

被引:21
作者
Curran, DP [1 ]
Gabarda, AE [1 ]
机构
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4020(98)01144-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reduction of 2-substituted 1,3-diiodopropane derivatives with tin hydride provides substituted cyclopropanes. The reaction occurs through a homolytic substitution of the 3-iodopropyl radical, which has a rate constant of about 5 x 10(5) s(-1) at 80 degrees C. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3327 / 3336
页数:10
相关论文
共 29 条
[1]  
BUMGARDNER CL, 1985, J AM CHEM SOC, V85, P73
[2]   BRIDGEHEAD-COUPLED BICYCLO[1.1.1]PENTANES - SYNTHESIS AND STRUCTURE [J].
BUNZ, U ;
POLBORN, K ;
WAGNER, HU ;
SZEIMIES, G .
CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (10) :1785-1790
[3]  
Curran D. P., 1991, COMPREHENSIVE ORGANI, V4, P715
[4]  
Curran D. P., 1991, COMPREHENSIVE ORGANI, V4, P779
[5]   Stereoselection at the steady state. Group selective radical cyclizations of substrates containing two radical precursors and one radical acceptor [J].
Curran, DP ;
Lin, CH ;
DeMello, N ;
Junggebauer, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :342-351
[6]   Tris(2-(perfluorohexyl)ethyl)tin hydride: A new fluorous reagent for use in traditional organic synthesis and liquid phase combinatorial synthesis [J].
Curran, DP ;
Hadida, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2531-2532
[7]   SUBSTRATE-CONTROLLED GROUP-SELECTIVE RADICAL CYCLIZATIONS - A NEW STRATEGY FOR STEREOCONTROLLED TRANSFORMATIONS OF DIASTEREOMERIC REACTIVE INTERMEDIATES [J].
CURRAN, DP ;
QI, HY ;
DEMELLO, NC ;
LIN, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (18) :8430-8431
[8]  
CURRAN DP, UNPUB
[9]   Stereoselection at the steady state by stereoconvergent reaction topography [J].
DeMello, NC ;
Curran, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :329-341
[10]   3-IODOPROPYL RADICAL - CLOSURE TO CYCLOPROPANE [J].
DRURY, RF ;
KAPLAN, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (07) :2217-2221