4+3 cycloaddition reactions of halogen-substituted cyclohexenyl oxyallylic cations

被引：18

作者：

Harmata, M ^{[1
]}

Shao, LX ^{[1
]}

Kürti, L ^{[1
]}

Abeywardane, A ^{[1
]}

机构：

[1] Univ Missouri, Dept Chem, Columbia, MO 65211 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 06期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(98)02629-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,6-Dibromo- and 2,2-dichlorocyclohexanone react with base in the presence of various dienes to give 4+3 cycloadducts in fair to good yields. Preliminary studies of the cycloadducts suggest that they are unstable and are recalcitrant to nucleophilic addition and cross-metathesis. However, the LAH reduction products undergo a quasi-Favorskii rearrangement upon treatment with potassium hydride and one cycloadduct derivative was dehalogenated using radical chemistry. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1075 / 1078

页数：4

共 23 条

[21] THE QUASI-FAVORSKII REARRANGEMENT .1. THE PREPARATION OF DEMEROL AND BETA-PETHIDINE [J].