Reactivity of a (Diazomethylene)phosphorane with Alkylating Agents and Lewis Acids; Synthesis of the First α‐Diazoalkylborates

Abstract

An electrophilic attack at the diazo carbon atom is postulated as initiating step in the Lewis acid catalyzed decomposition of diazo compounds. Experimental detection of such primary adducts has now been accomplished with the electronically stabilized (diazomethylene)phosphorane 1, which, for example, gives the salt 2 upon reaction with mercury(II) chloride, and the borate 3 upon reaction with tetrahydrofuran-borane.