Superiority of very weakly basic amines as catalysts for alpha-proton abstraction via iminium ion formation

…, HE Ferran Jr, MJ Gula, TA Spencer

Index: Roberts, Rex D.; Ferran, Herbert E.; Gula, Michael J.; Spencer, Thomas A. Journal of the American Chemical Society, 1980 , vol. 102, # 23 p. 7054 - 7058

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Citation Number: 19

Abstract

Abstract: Catalysis of the conversions of beta-keto1 6 and beta-acetoxy ketone 7 to enone 3 via amine-carbonyl condensation has been studied by using eight nontertiary amines having a pK, range from 10.61 to 1.22, including the very weakly basic 3, 3, 4, 4- tetrafluoropyrrolidine (pK,= 4.05) and 1, 1, 1, 3, 3, 3-hexafluoroisopropylamine (pK,= 1.22). Kinetic terms reflecting rate-determining alpha-proton abstraction via iminiup ion formation ...