The Journal of Organic Chemistry

Nucleophilic substitution at an acetylenic carbon. Mechanistic and synthetic study of the reactions of phosphines with haloacetylenes

JI Dickstein, SI Miller

文献索引：Dickstein,J.I.; Miller,S.I. Journal of Organic Chemistry, 1972 , vol. 37, p. 2168 - 2175

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被引用次数: 17

摘要

A synthetic route to ethynylphosphonium salts from haloacetylenes, phenylhaloacetylenes, but not alkylhaloacetylenes is described. These salts are electrophiles; when phenylethynyltriphenylphosphonium bromide is treated with tributylphosphine in acetonitrile, the a, p-bis (tributy1phosphonium) styrene dibromide is formed. Rate data for the second- order reactions of several systems in DMF are (AH*, kcal/mol; AS*, eu; k, M-'sec-'at 36”): ...