CONFIGURATIONALLY AND CONFORMATIONALLY HOMOGENEOUS CYCLIC N-ARYL SULFIMIDES .3. STEREOCHEMISTRY OF REARRANGEMENT

被引：8
作者：
CLAUS, PK
RIEDER, W
VIERHAPPER, FW
BAILER, J
机构：
[1] Institut für Organische Chemie der Universität Wien, A-1090 Wien
来源：
TETRAHEDRON | 1979年 / 35卷 / 11期
关键词：
D O I：
10.1016/0040-4020(79)85031-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Configurationally and conformationally homogeneous thiane- and trans- and cis-1-thiadecalin-1-N-p-chlorophenyl imides were rearranged to the corresponding 2-(2'-amino-5'-chlorophenyl)-sulfides and the configurations of the products were assigned by 1H-NMR spectroscopy. If sterically unhindered, rearrangements proceeded with a high degree (95%) of stereospecifity: sulfimides with equatorial S-N-bond gave rearranged products with axial, sulfimides with axial S-N-bond gave rearranged products with equatorial aryl substituent. The proposed concerted mechanism via a cyclic transition state is supported by these results. © 1979.
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收藏
页码：1373 / 1383
页数：11
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