Synthesis and novel reactivity of halomethyldimethylsulfonium salts
Synthesis and novel reactivity of halomethyldimethylsulfonium salts
复制标题
卤甲基二甲基锍盐的合成及新型反应性
DOI：
10.1021/jo000015f
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发表时间：
2000
期刊：
影响因子：
--
通讯作者：
W. Dolbier
中科院分区：
文献类型：
--
作者：
Y. Xu;M. Fletcher;W. Dolbier
碘甲基-、氯甲基-和氟甲基二甲基锍盐4 b-d已被合成，并被观察到是高度反应性的分子，其在其反应性的性质方面表现出非凡的多样性，经历容易的直接取代（S（N）2）反应，但也对电子转移反应高度敏感。循环伏安法实验表明，碘甲基二甲基锍化合物，4 b，是一个有效的电子受体，甚至超过了全氟正烷基碘的反应能力。碘-和氯甲基二甲基锍盐，4 b，c，以及类似的碘甲基三甲基铵盐，3a，被证明是反应性SET受体。
Iodomethyl-, chloromethyl-, and fluoromethyldimethylsulfonium salts, 4b-d, have been synthesized and are observed to be highly reactive molecules that exhibit extraordinary diversity with respect to the nature of their reactivity, undergoing facile direct substitution (S(N)2) reactions, but also being highly susceptible to electron-transfer reactions. Cyclic voltametry experiments indicated that the iodomethyldimethylsulfonium compound, 4b, is a potent electron acceptor, even surpassing the reactivity of perfluoro-n-alkyl iodides in that capacity. The iodo- and chloromethyldimethylsulfonium salts, 4b,c, as well as the analogous iodomethyltrimethylammonium salt, 3a, are shown to be reactive SET acceptors.