Tetrahedron letters

A novel reaction of N-phenylthiocaprolactam: The α-sulfenylation of ketones under mild conditions

G Foray, AB Peñéñory, RA Rossi

Index: Foray, Gabriela; Penenory, Alicia B.; Rossi, Roberto A. Tetrahedron Letters, 1997 , vol. 38, # 12 p. 2035 - 2038

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Citation Number: 19

Abstract

N-phenylthiocaprolactam (2) reacts with the enolate anions of aliphatic, aromatic or cyclic ketone 1a-e, to give the corresponding α-phenylthioketones 3a-e. This reaction proceeds with high yields of monosulphenylation (80–97%) in DMSO under mild conditions (potassium ter-butoxide, 25° C, 10 min).

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