The Journal of Organic Chemistry

Quasi-concerted allylic rearrangement in the reaction of allylic chlorides with methyltin tris (methanethiolate)

HE Katz, WH Starnes Jr

文献索引：Katz, Howard Edan; Starnes, William H. Journal of Organic Chemistry, 1984 , vol. 49, # 15 p. 2758 - 2761

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被引用次数: 4

摘要

trans-6-Chloro-4-decne (4), 3-chloro-l-heptene (7), and trans-l-chloro-2-heptene (9) are converted quantitatively into allylic methyl sulfides upon treatment with a molar equivalent of methyltin tris (methanethio1ate) at 70 OC in benzene-dichloromethane. Unlike the reactions of sodium thiolates with straight chain allylic chlorides, these nucleophilic displacements are accompanied by very significant amounts of allylic rearrangement, with the yields of ...