Amino-acids and peptides. Part II. A new method for preparing diazodiphenylmethane and related compounds

Abstract

Diazodiphenylmethane has been prepared from benzophenone hydrazone by oxidation with peracetic acid in the presence of a base and a trace of iodine. Two variants of the process are described: (a) benzophenone hydrazone in an organic solvent is oxidised with peracetic acid in the presence of 1,1,3,3-tetramethylguanidine and a trace of iodine; (b) a solution of benzophenone hydrazone, in a two-phase organic solvent–water mixture, is oxidised by adding peracetic acid and sodium hydroxide simultaneously and equivalently at pH ca. 10 in the presence of a phase-transfer catalyst and a trace of iodine. The preparation of a variety of aryldiazoalkanes is reported.