KINETICS OF HYDROLYSIS AND DISPLACEMENT REACTIONS OF BETA,BETA-'-DICHLORODIETHYL SULFIDE (MUSTARD GAS) AND OF BETA-CHLORO-BETA-'-HYDROXYDIETHYL SULFIDE (MUSTARD CHLOROHYDRIN)
KINETICS OF HYDROLYSIS AND DISPLACEMENT REACTIONS OF BETA,BETA-'-DICHLORODIETHYL SULFIDE (MUSTARD GAS) AND OF BETA-CHLORO-BETA-'-HYDROXYDIETHYL SULFIDE (MUSTARD CHLOROHYDRIN)
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DOI：
10.1021/ja01172a076
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发表时间：
1949-01-01
影响因子：
15
通讯作者：
SWAIN, CG
中科院分区：
文献类型：
--
作者：
BARTLETT, PD;SWAIN, CG
1937年，Roberts和Kimball首次假设了乙炔溴离子(I)的存在及其在溴化反应中的作用。Winstein和Lucas3在1939年提供了乙炔溴离子在/3-溴烷基化合物的置换反应中的作用。在第二次世界大战期间，美国工人认识到，非常类似的乙烯磺酸离子（II）为/ 3,3 '-二氯二乙基硫化物（芥子气，III）的一级置换反应提供了一个有吸引力的解释，这是任何伯烷基氯都没有表现出来的一种置换动力学。奥格斯顿观察到，他对这种反应的广泛研究是芥末项目中使用的大多数想法的基础
Introduction The existence of the ethylenebromonium ion (I) and its participation in bromination reactions were first postulated in 1937 by Roberts and Kimball. 2 An elegant demonstration of the participation of such ions in displacement re-actions of/3-bromoalkyl compounds was provided by Winstein and Lucas3 in 1939. During World War II it was recognized by American workers that the closely analogous ethylenesulfonium ion (II) offered an attractive explanation of the first-order displacement reactions4 of/3,/3'-dichloro-diethyl sulfide (mustard gas, III) a type of dis-placement kinetics not shown by any primary alkyl chloride. 5 Ogston, whose extensive studies of this reaction were the basis of most ofthe ideas used in the mustard program, observed