The Wagner-Meerwein rearrangement, 1 a carbon-to-carbon 1,2-migration, typically of an alkyl, vinyl, or aryl group to an adjacent carbocationic center, as depicted in eq 1, requires

A simple method for the synthesis of carbamate-protected guanidines from primary amines is described. A variety of thioureas derived from primary amines and isothiocyanates react with the Burgess reagent to give the corresponding guanidines via either a stepwise or one-pot procedure. By tuning the carbamoyl units of isothiocyanates and the Burgess reagent, differentially N,N'-diprotected guanidines can be obtained. Selective deprotection of the products affords N-monoprotected guanidines.

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