The Journal of Organic Chemistry

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

FG Bordwell, DL Hughes

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

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被引用次数: 51

摘要

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- ...