A Simple Method for Generation of Diazocompounds in an Aqueous Two-Phase System

Abstract

Decomposition of tosylhydrazones of carbonyls in a basic medium is one of the most important methods for synthesis of diazocompounds (Bamford-Stevens reaction)¹. This reaction with arylaldehyde, arylalkyl- and diaryl ketone tosylhydrazones is usually carried out in the presence of sodium alkoxides in alcohols, glycols, their ethers or in pyridine. Diazocompounds stabilized by electron withdrawing groups can be generated under milder conditions (diluted aq NaOH solutions or basic Al₂O₃). The standard conditions of the Bamford-Stevens reaction are not suitable for the synthesis of diazoalkanes derived from aliphatic aldehydes and ketones.