Carbanions. 20. Rearrangements in reactions of 5-chloro-4, 4-diphenyl-2-pentyne, 1-chloro-5, 5-dimethyl-2, 2-diphenyl-3-hexyne, and 5, 5-dimethyl-2, 2-diphenyl-3- …

E Grovenstein Jr, KW Chiu, BB Patil

Index: Grovenstein,E.; Chiu,K.W.; Patil,B.B. Journal of the American Chemical Society, 1980 , vol. 102, p. 5848

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Citation Number: 15

Abstract

Abstract: Lithium reacts with 5-chloro-4, 4-diphenyl-2-pentyne (7a) and with l-chloro-5, 5- dimethyl-2, 2-diphenyl-3-hexyne (7b) in THF at-75 OC to give 2, 2-diphenyl-3- pentynyllithium (14a) and 5, 5-dimethyl-2, 2-diphenyl-3-hexynyllithium (14b), respectively; when the THF solutions of these organolithium reagents are warmed to 0 OC,[1, 2] migration of the acetylenic group of each occurs to produce 1, I-diphenyl-3-pentynyllithium (16a) ...