Effective precursors for sulfur monoxide formation

被引:36
作者
AbuYousef, IA
Harpp, DN
机构
[1] MCGILL UNIV,DEPT CHEM,MONTREAL,PQ H3A 2K6,CANADA
[2] AL ALBAYT UNIV,DEPT CHEM,MAFRAG 25113,JORDAN
关键词
D O I
10.1021/jo9709864
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
When triphenylmethanesulfenyl chloride (12) (or its thio 13 or dithio homolog 14) are treated with hindered olefins 15 and 16, thiiranes 10 and 11, are produced in high isolated yields (ca. 94%). Treatment of 10 and 11 with m-chloroperoxybenzoic acid (m-CPBA) leads to the formation of thiirane 1-oxides 8 and 9 (99% isolated yields). The structures of 8-11 were established by H-1 and C-13 NMR, mass spectrometry as well as by X-ray. Thermal decomposition of either 8 or 9 smoothly delivers sulfur monoxide to various 1,3-dienes giving cyclic sulfoxides in good yield. A variety of conditions were employed to optimize the yield of the trapped adducts.
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页码:8366 / 8371
页数:6
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