The Journal of Organic Chemistry

Condensations at methyl groups of phenyl o-and p-tolyl sulfones with electrophilic compounds by sodium amide. Truce-Smiles rearrangement

GP Crowther, CR Hauser

Index: Crowther,G.P.; Hauser,C.R. Journal of Organic Chemistry, 1968 , vol. 33, # 6 p. 2228 - 2233

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Citation Number: 10

Abstract

Ionizations of methyl hydrogens of phenyl 0-and p-tolyl sulfones were effected by sodium amide in liquid ammonia to form sodio salts, which were condensed with benzyl chloride, 1, 4-dibromobutane, benzophenone, and methyl benzoate to give corresponding derivatives. Ionization of the phenyl o-tolyl sulfone occurred more slowly than that of the para isomer. The addition reactions of the sodio salts with benzophenone were kinetically controlled. ...