Rearrangement of unactivated N-alkyl- O-benzoyl hydroxamic acid derivatives with phosphazene bases

Abstract

The phosphazene super bases BTPP 5 , P-2- t Bu 6 , and P-4- t Bu 7 mediate the rearrangement of unactivated N-alkyl- O-benzoyl hydroxamic acid derivatives 8 , 11a– f , 13 and 16 to give 2-benzoyloxy amides 9 , 12a– f , 14 and 17 . The rate of reaction was found to be dependant upon the steric nature of the N-alkyl substituent.