Reactions of 9-substituted fluorenide carbanions with allyl chlorides by SN2 and SN2'mechanisms

FG Bordwell, AH Clemens…

文献索引：Bordwell, Frederick G.; Clemens, Anthony H.; Cheng, Jin-Pei Journal of the American Chemical Society, 1987 , vol. 109, # 6 p. 1773 - 1782

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被引用次数: 27

摘要

Abstract: The average ratio of SN2 rate constants for benzyl chloride vs. allyl chloride reacting with 9-substituted fluorenide carbanions, 9-G-FI-(G= Me, PhS, Ph, o-tol, or t-Bu), in Me2S0 solution is 2.3, which is close to the ratio previously observed for reactions of smaller nucleophiles with more localized charges, such as iodide ion, in various solvents. Brernsted plots of log k vs. pKHA (both in Me2SO) are used to calculate reactivity values (r) for 9-G-Fl ...