Iodosulfonation of alkenes with benzenesulfinic acid -: N-iodosuccinimide -: Facile preparation of α,β-unsaturated sulfones

被引：12

作者：

Wolff, Russell R. ^{[1
]}

Basava, Vikram ^{[1
]}

Giuliano, Robert M. ^{[1
]}

Boyko, Walter J. ^{[1
]}

Schauble, J. Herman ^{[1
]}

机构：

[1] Villanova Univ, Dept Chem, Villanova, PA 19085 USA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 2006年 / 84卷 / 04期

关键词：

iodosulfonation; vinyl sulfones; benzenesulfinic acid; N-iodosuccinimide; dehydroiodination;

D O I：

10.1139/V06-051

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of alkenes and alkenols with N-iodosuccinimide (NIS) and benzenesulfinic acid in dichloromethane at room temperature affords vic-iodophenylsulfonyl adducts in good to high yields. Treatment of the iodosulfones with neutral alumina in dichloromethane at room temperature results in dehydroiodination to give the corresponding vinyl sulfones in high yield and purity by this convenient two-step procedure. Application of the iodosulfonation-dehydroiodination sequence to allylic alcohols and silyl ethers gave gamma-oxygenated, alpha,beta-unsaturated phenylsulfones, while the attempted iodosulfonation of glycals, as intermediates to vinyl sulfones, resulted in addition of benzenesulfinic acid with double bond shift (Ferrier rearrangement).

引用

页码：667 / 675

页数：9

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