SECONDARY REACTIONS OF SULFENES FROM SULFONYL CHLORIDES AND TERTIARY-AMINES .1. ON THE COMPETING FORMATION OF SULFENE TRIALKYLAMINE S,N-ADDUCTS AND C,N-ADDUCTS

被引：17

作者：

OPITZ, G

RIETH, K

EHLIS, T

机构：

[1] Organisch-Chemisches Institut, Universität Heidelberg, Heidelberg, D-6900

来源：

CHEMISCHE BERICHTE | 1990年 / 123卷 / 07期

关键词：

2‐Trimethylammonio‐2‐propanesulfinate; Amine–sulfene adducts; Episulfones; Sulfene–amine adducts; Sulfones; α‐chloro‐;

D O I：

10.1002/cber.19901230717

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Secondary Reactions of Sulfenes from Sulfonyl Chlorides and Tertiary Amines, 1. ‐ On the Competing Formation of Sulfene ‐ Trialkylamine S,N‐ and C,N‐Adducts Phenylmethanesulfonyl chloride (1a) reacts with an excess of triethylamine in acetonitrile solution at ‐40°C to give stilbene episulfone (9a, 95%) via the phenylsulfene–triethylamine S,N‐adduct 1ah. With trimethylamine and quinuclidine the yield of stilbene is reduced by the additional formation of (benzylsulfonyl)phenylsulfene–amines S,N‐adducts 11ag and 11ae and C,N‐adducts 15ag and 15ae which was proven by reaction with dimethylamine to 16 and by hydrolysis to 17–19, respectively. 1d reacts with triethylamine yielding 94% of α‐chloro sulfones 4s and 6d via pentamethylenesulfene–triethylamine S,N‐adduct 5dh, with trimethylamine, however, C,N‐adduct 12dg is obtained which is easily oxidized to 20dg (47%). The air‐sensitive dimethylsulfene–trimethylamine C,N‐adduct 12cg was isolated and characterized. Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

引用

页码：1563 / 1569

页数：7

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