The Journal of Organic Chemistry

Titanium trichloride reduction of substituted N-hydroxy-2-azetidinones and other hydroxamic acids

PG Mattingly, MJ Miller

Index: Mattingly, Phillip G.; Miller, Marvin J. Journal of Organic Chemistry, 1980 , vol. 45, # 3 p. 410 - 415

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Citation Number: 106

Abstract

A mild method of reduction of the N-0 bond of substituted N-hydroxy-2-azetidinones was required to complete a hydroxamic acid mediated synthesis of substituted (I-lactams. Of the several reduction methods studied, most either failed to reduce the NO bond, cleaved the 2- azetidinone ring, or were inefficient and inconvenient. However, buffered titanium trichloride cleanly reduced the N-0 bond of the N-hydroxy-2-azetidinones under conditions ...