Ruthenium tetroxide oxidation of N-acylated alkylamines: A new general synthesis of imides.

KENI TANAKA, S YOSHIFUJI, Y NITTA

Index: Tanaka, Ken-Ichi; Yoshifuji, Shigeyuki; Nitta, Yoshihiro Chemical & Pharmaceutical Bulletin, 1987 , vol. 35, # 1 p. 364 - 369

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Citation Number: 27

Abstract

Oxidation of various N-acylalkylamines with ruthenium tetroxide (RuO 4) was systematically investigated. N-Acylalkylamines having an electron-donating group at the α-or β-position with respect to amide nitrogen or an electron-donating alkyl function in the acyl group were smoothly oxidized to the corresponding imides in excellent yields. On the other hand, N- acylalkylamines having an electron-withdrawing group were not oxidized at all, and most ...