CONCERNING THE REACTION OF ANTI-BENZENE DIOXIDE WITH VARIOUS NUCLEOPHILES

被引：7

作者：

ESSER, T ^{[1
]}

FARKAS, F ^{[1
]}

MANGHOLZ, S ^{[1
]}

SEQUIN, U ^{[1
]}

机构：

[1] UNIV BASEL,INST ORGAN CHEM,ST JOHANNS RING 19,CH-4056 BASEL,SWITZERLAND

来源：

TETRAHEDRON | 1994年 / 50卷 / 12期

关键词：

D O I：

10.1016/S0040-4020(01)90392-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

trans-3,4:5,6-Diepoxycyclohex-1-ene (anti-benzene dioxide) (5) was brought into reaction with several S, O, and C nucleophiles. S and O nucleophiles gave the bis-adducts stemming from independent reaction of the two epoxy functions. C nucleophiles, on the other hand, led to 1,4-addition products. A deuterium labelling experiment showed that BuLi added to the vinyloxirane part of 5 rather than to the conjugated diepoxide function, yielding the cis-adduct. Cuprates gave - as expected - predominatly the trans-products.

引用

页码：3709 / 3720

页数：12

共 27 条

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