Demonstration of reversible C-C bond cleavage in oxiranylcarbinyl radicals.

被引:10
作者
Marples, BA [1 ]
Rudderham, JA [1 ]
Slawin, AMZ [1 ]
Edwards, AJ [1 ]
Hird, NW [1 ]
机构
[1] SMITHKLINE BEECHAM PHARMACEUT, HARLOW CM19 5AW, ESSEX, ENGLAND
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(97)00673-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The incorporation of a stereochemical probe into aryl substituted oxiranylcarbinyl radicals has demonstrated that the C-C bond cleavage in these systems is reversible, and that it can occur even when no products of C-C cleavage are obtained. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3599 / 3602
页数:4
相关论文
共 17 条
[1]  
BOWMAN WR, 1992, TETRAHEDRON, V48, P6883
[2]   RADICAL-INDUCED FRAGMENTATIONS OF KETOEPOXIDES [J].
BREEN, AP ;
MURPHY, JA ;
PATTERSON, CW ;
WOOSTER, NF .
TETRAHEDRON, 1993, 49 (46) :10643-10654
[3]  
CORSER DA, 1992, SYNLETT, P987
[4]   1-ALKENYLCYCLOALKOXY RADICAL CHEMISTRY - A 2-CARBON RING EXPANSION METHODOLOGY [J].
GALATSIS, P ;
MILLAN, SD ;
FABER, T .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1215-1220
[5]   USE OF IODOBENZENE DIACETATE FOR THE SYNTHESIS OF ALPHA-IODOEPOXIDES [J].
GALATSIS, P ;
MILLAN, SD .
TETRAHEDRON LETTERS, 1991, 32 (51) :7493-7496
[6]   ASPECTS OF STEREOCHEMISTRY .1. STEREOSPECIFICITY IN FORMATION OF EPOXIDES FROM CYCLIC ALLYLIC ALCOHOLS [J].
HENBEST, HB ;
WILSON, RAL .
JOURNAL OF THE CHEMICAL SOCIETY, 1957, (MAY) :1958-1965
[7]   COMPUTER-ASSISTED MECHANISTIC EVALUATION OF ORGANIC-REACTIONS .17. FREE-RADICAL CHAIN REACTIONS [J].
LAIRD, ER ;
JORGENSEN, WL .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :9-27
[8]   REGIOSELECTIVITY OF RADICAL-INDUCED BOND CLEAVAGES IN EPOXIDES [J].
MURPHY, JA ;
PATTERSON, CW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04) :405-410
[9]   PHOTOLYSIS OF ORGANIC NITRITES .5. INTRAMOLECULAR ALKOXIDE RADICAL ADDITION TO A DOUBLE BOND [J].
NUSSBAUM, AL ;
OLIVETO, EP ;
WAYNE, R ;
YUAN, E ;
ZAGNEETK.O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (06) :1070-&
[10]   SYNTHESIS OF CARBOCYCLIC SYSTEMS VIA RADICAL-INDUCED EPOXIDE FRAGMENTATION [J].
RAWAL, VH ;
NEWTON, RC ;
KRISHNAMURTHY, V .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) :5181-5183