Journal of the American Chemical Society

Neighboring Carbon and Hydrogen. XXVII. Ar1-5 Aryl Participation and Tetralin Formation in Solvolysis1, 2

R Heck, S Winstein

Index: Winstein; Baird Journal of the American Chemical Society, 1957 , vol. 79, p. 756

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Citation Number: 30

Abstract

It is possible, by suitable choice of structure and solvent, to arrange for participation of &aryl groups in solvolysis of 4-aryl-1-butyl p-bromobenzenesulfonates. When the aryl group is activated by one p-or two o, p-methoxyl groups, the participation is Arl-5 in type; a spiro- carbonium ion is produced by anchimerically assisted ionization of the 4-aryl-1-butyl bromobenzenesulfonate. Rearrangement of the spiro-carbonium ion intermediate and ...