Degradative Rearrangements of N-(t-Butyloxycarbonyl)-O-methanesulfonyl-hydroxamic Acids: A Novel, Reagent-Based Alternative to the Lossen Rearrangement1

JA Stafford, SS Gonzales, DG Barrett…

Index: Stafford, Jeffrey A.; Gonzales, Stephen S.; Barrett, David G.; Suh, Edward M.; Feldman, Paul L. Journal of Organic Chemistry, 1998 , vol. 63, # 26 p. 10040 - 10044

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Citation Number: 25

Abstract

During the course of our research efforts, we required a multigram conversion of cyclopentenyl carboxylic acid 1 to the corresponding amine 2 (eq 1). Application of the Curtius rearrangement2 on laboratory microscale satisfactorily delivered the desired product. However, due to the scale on which we needed to operate the Curtius reaction and the safety hazard3 associated with the involvement of low molecular-weight acyl azides, ...