Benzylic metallation of thiobenzamides and thionaphthamides

D Ach, V Reboul, P Metzner

Index: Ach, David; Reboul, Vincent; Metzner, Patrick European Journal of Organic Chemistry, 2002 , # 15 p. 2573 - 2586

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Citation Number: 14

Abstract

Abstract Various secondary thiobenzamides and thionaphthamides have been prepared, and features of their conformations [orthogonality of the arene and thioamide planes,(Z) geometries in solution etc.] have been determined. Deprotonation with sec-butyllithium selectively provided either the monoanion or the dianion, according to the stoichiometry of the base. The monoanion reacted with soft electrophiles (alkyl halides) through the sulfur ...