Stabilization of carbanions by polarization of alkyl groups on nonadjacent atoms

…, GE Drucker, GJ McCollum

Index: Bordwell, Frederick G.; Drucker, George E.; McCollum, Gregory J. Journal of Organic Chemistry, 1982 , vol. 47, # 13 p. 2504 - 2510

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Citation Number: 40

Abstract

Equilibrium acidities in dimethyl sulfoxide solution have been found to increase along the series Me, Et, i-Pr, t-Bu for 9-substituted fluorenes when the alkyl group, R, is separated from the fluorene ring by a CHz, S, or SO2 moiety. This is a reversal of the effect observed when R is attached directly to the fluorene ring. Separation of the t-Bu group from the fluorene ring by a second CH2 moiety causes the acidifying effect to disappear. A stabilizing, through- ...