Journal of the American Chemical Society

Reactions of aromatic radical anions. III. Evidence for an alkyl radical-radical anion combination mechanism for alkylation of sodium naphthalenide with alkyl halides

GD Sargent, GA Lux

Index: Sargent,G.D.; Lux,G.A. Journal of the American Chemical Society, 1968 , vol. 90, p. 7160 - 7162

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Citation Number: 51

Abstract

Subsequent reduction of the resulting free radical 10 yields a delocalized carbanion (ll), which can attack another molecule of alkyl halide to yield products 5 and 6 or abstract a proton from solvent to form 7 and 8. Hoijtinks suggests that alkylation is initiated by addition of an alkyl free radical to a molecule of naphthalene, which is produced in the charge- transfer reaction of 1 with the alkyl halide (2). The resulting delocalized free radical 10 is ...