1-SUBSTITUTED 1,3-DIHYDROISOTHIANAPHTHEN-2,2-DIOXIDES - PREPARATION AND USE AS ORTHO-QUINODIMETHANE PRECURSORS IN INTRA-MOLECULAR CYCLOADDITIONS - PRELIMINARY COMMUNICATION

被引:64
作者
OPPOLZER, W
ROBERTS, DA
BIRD, TGC
机构
[1] Département de Chimie Organique, Université de Genève, Genève
关键词
D O I
10.1002/hlca.19790620630
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
1,3‐Dihydroisothianaphthen‐2,2‐dioxide 1 was readily converted to the 1‐substituted sulfones 3 by deprotonation and subsequent electrophilic attack (Scheme 3 and Table). The appropriate 1‐alkenyl‐ and 1‐alkenoyl‐sulfones 3 on heating at 213° to 240° underwent SO2‐extrusion to give, via the non‐isolated (E)‐quinodimethanes II (Scheme 1), polycyclic products such as 4, 6 and 7 in good yields (Schemes 4 and 5). On the other hand, thermolysis of the 1‐alkenoyl‐1‐thioether sulfones 9 furnished mainly the isochromenes 10 (Scheme 6). Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim
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页码:2017 / 2021
页数:5
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