Carbanions. XI. Reactions of 4-chloro-1, 1, 1-triphenylbutane, 5-chloro-1, 1, 1-triphenylpentane, and 1, 1, 1-triphenylethane with alkali metals. 1, 4 and 1, 5 Migration …

E Grovenstein Jr, JA Beres, YM Cheng…

Index: Grovenstein,E. et al. Journal of Organic Chemistry, 1972 , vol. 37, # 9 p. 1281 - 1292

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Citation Number: 18

Abstract

Whereas 1, 2 migrations of phenyl are known in carbanions, corresponding 1, 4 and l, 5 migrations have not been reported. In the present work such rearrangements were looked for in the reactions of 4-chloro-and S-chlorol, l, l-triphenylalkanes with alkali metals. Reaction of 4-chloro-l, lJl-triphenylbutane with lithium in tetrahydrofuran (THF) at-50 to- 60'gives 4, 4, 4-triphenylbutyllithium; when the latter is warmed to 25" l, l, l-triphenylbutane ...