The cleavage of caryophyllene oxide catalysed by tetracyanoethylene

被引：48

作者：

Collado, IG ^{[1
]}

Hanson, JR ^{[1
]}

MaciasSanchez, AJ ^{[1
]}

机构：

[1] UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND

来源：

TETRAHEDRON | 1996年 / 52卷 / 23期

关键词：

D O I：

10.1016/0040-4020(96)00367-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cleavage of caryophyllene oxide under novel, mild and clean conditions, using tetracyanoethylene as a catalyst, is described. Alcoholysis leads to clovenol-2-ether derivatives as major products. When dipolar aprotic solvents were used, rearrangement products were not formed and compounds from elimination reaction were obtained. The ratio of cyclization to elimination products reflects the extent to which the partially delocalized carbocation may be stabilized by the nucleophilic solvent. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7961 / 7972

页数：12

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