Nitrosamides derived from peptide models: their preparations and chemical behavior.

N-Acyl alpha-amino acids have been nitrosated to yield the nitrosamides, which are virtually stable at room temperature, but are thermolysed in refluxing benzene or methanol. The corresponding carboxylates of these nitrosamides rearrange rapidly at room temperature to generate diazoalkane- and/or diazoacylate-type intermediates, which are good alkylating agents. Rate constants for the decomposition of the nitrosamide, N-acetyl-N-nitroso-D,L-phenylalanine, have been determined.