Direct relationship between nucleophilicity and basicity in SN2 reactions of fluorenyl anions with benzyl chloride in dimethyl sulfoxide solution

FG Bordwell, DL Hughes

Index: Bordwell, Frederick G.; Hughes, David L. Journal of Organic Chemistry, 1980 , vol. 45, # 16 p. 3314 - 3320

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Citation Number: 51

Abstract

The rates of reactions for nine 9-substituted fluorenyl anions, 9-G-Fl-(G= CN, C02Me, PhS02, PhS, Ph, PhO, PhCH2, Me, t-Bu), reacting with benzyl chloride in Me2S0 solution have been measured. For 9-CN-Flthe rates increased with solvent in the order N- methylpyrrolidin-2-one (NMP)< Me2S0< MeOH< EtOH< t-BuOH. Ely the introduction of substituents into the 2-and 2, 7-position (s) of the fluorene ring for 9-CO2Me-F1-and 9-Me- ...