Nature of N-bromosuccinimide in basic media: the true oxidizing species in the Hofmann rearrangement

…, LE Fredenburgh, RA Reamer, RD Larsen…

Index: Senanayake, Chris H.; Fredenburgh, Laura E.; Reamer, Robert A.; Larsen, Robert D.; Verhoeven, Thomas R.; Reider, Paul J. Journal of the American Chemical Society, 1994 , vol. 116, # 17 p. 7947 - 7948

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Citation Number: 26

Abstract

The Hofmann rearrangement is among the oldest reactions in organic synthesis1 and is often used for the introduction of the amine functionality.* Practical reagents for this transformation, however, are still lacking. For example, the classical means for converting a primary carboxamide to an amine using an alkaline solution of bromine can be unsatisfactory and~ nreliable.~ Numerous modifications of this protocol have extended its ...