LEWIS ACID MEDIATED REACTION OF N-PHENYL-S-(4-METHYLPHENYL)SULFOXIMIDOYL CHLORIDE WITH ALKENES

被引：15

作者：

HARMATA, M

CLAASSEN, RJ

BARNES, CL

机构：

[1] Department of Chemistry, University of Missouri-Columbia, Columbia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 17期

关键词：

D O I：

10.1021/jo00017a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of N-phenyl-S-(4-methylphenyl)sulfoximidoyl chloride (1) with alkenes in the presence of aluminum chloride leads to 2,1-benzothiazines in good yield. The reaction is regioselective, sometimes highly stereoselective, and is stereospecific with respect to alkene geometry. The mechanism can be formulated as a concerted cycloaddition between the iminosulfonium species 2 and the alkene to form a sigma-complex that subsequently rearomatizes to give the product.

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页码：5059 / 5062

页数：4

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