Synthesis and properties of tetrazolium N-phenacylides

Abstract

A number of isomeric tetrazolium 1-phenacylides (6)[type (A)] and 3-phenacylides (7)[type (B)] have been prepared by deprotonation of the corresponding salts (3) and (4) and submitted to standard ylide reactions. A comparison of their physicochemical properties as well as their reactivity toward alkali hydroxide and several electrophiles demonstrates that the 3-tetrazoliumyl system as in (B) exerts a stronger electron-withdrawing influence than the 1-tetrazoliumyl system as in (A). Phenacylides of type (C) could not be isolated.