Intramolecular cyclisations of hydroxylamines derived from limonene: Reverse-cope or acid-catalysed reactions?

被引：11
作者：
Coogan, MP
Knight, DW
机构：
[1] Department of Chemistry, Cardiff University, Cardiff, CF1 3TB
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 35期
基金：
英国工程与自然科学研究理事会;
关键词：
D O I：
10.1016/0040-4039(96)01362-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intramolecular cyclisations of cis-4-ethenylcyclohexyl hydroxyl- amines [e.g. 3 derived from limonene] proceed via a reverse-Cope mechanism rather than an acid-catalysed process, as recently reported. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：6417 / 6420
页数：4
相关论文
共 20 条
[1]   ISOQUINUCLIDINE DERIVATIVES FROM LIMONENE [J].
BAKUNOV, SA ;
DENISOV, AY ;
TKACHEV, AV .
TETRAHEDRON, 1995, 51 (31) :8565-8572
[2]   NITRONES AND OXAZIRIDINES .22. PREPARATION AND CYCLIZATION OF SOME DELTA,EPSILON-UNSATURATED HYDROXYLAMINES [J].
BLACK, DSC ;
DOYLE, JE .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (10) :2317-2322
[3]   REVERSE COPE ELIMINATION-REACTIONS .1. MECHANISM AND SCOPE [J].
CIGANEK, E ;
READ, JM ;
CALABRESE, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5795-5802
[4]   REVERSE COPE ELIMINATION-REACTIONS .2. APPLICATION TO SYNTHESIS(1) [J].
CIGANEK, E .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5803-5807
[5]  
CUSMANO G, 1910, GAZZ CHIM ITAL, V40, P122
[6]  
CUSMANO G, 1910, GAZZ CHIM ITAL, V40, P602
[7]  
CUSMANO G, 1910, GAZZ CHIM ITAL, V40, P525
[8]  
DAMBROSIO A, 1932, GAZZ CHIM ITAL, V62, P271
[9]   A TANDEM SYNTHESIS OF (+/-)-EUPHOCOCCININE AND (+/-)-ADALINE [J].
DAVISON, EC ;
HOLMES, AB ;
FORBES, IT .
TETRAHEDRON LETTERS, 1995, 36 (49) :9047-9050
[10]   N-ALKENYL NITRONE DIPOLAR CYCLOADDITION ROUTES TO PIPERIDINES AND INDOLIZIDINES .7. HYDROXYLAMINE ALKYNE CYCLIZATIONS - FORMATION OF CYCLIC NITRONES AND APPLICATION TO THE SYNTHESIS OF THE PROPOSED STRUCTURE FOR (+/-)-ACACIALACTAM [J].
FOX, ME ;
HOLMES, AB ;
FORBES, IT ;
THOMPSON, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23) :3379-3395
12