Ruthenium tetroxide oxidation of N-alkyllactams.

S YOSHIFUJI, Y ARAKAWA, Y NITTA

Index: Yoshifuji, Shigeyuki; Arakawa, Yukimi; Nitta, Yoshihiro Chemical & Pharmaceutical Bulletin, 1987 , vol. 35, # 1 p. 357 - 363

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Citation Number: 19

Abstract

Ruthenium tetroxide (RuO 4) oxidation of N-alkyllactams proceeded regioselectively depending on the size of lactam ring, except for the seven-membered ring. Four-and eight- membered N-methyl-and N-ethyllactams were oxidized at the exocyclic α-carbon adjacent to nitrogen to produce the N-acyllactams and NH-lactams, while five-and six-membered lactams underwent endocyclic oxidation to yield the cyclic imides. Oxidation of seven- ...