The reaction of diols with triphenylphosphine and di-isopropyl azodicarboxylate. Part 2. Formation of cyclic phosphoranes from 1,5–1,12-diols

Abstract

Triphenylphosphine and di-isopropyl azodicarboxylate react with pentane-1,5-diol, hexane-1,6-diol, heptane-l,7-diol, octane-1,8-diol, decane-1,10-diol, and dodecane-1,12-diol in tetrahydrofuran at 0 °C to give large-ring cyclic dioxytriphenylphosphoranes that appear to be oligomeric. Such phosphoranes undergo exchange reactions with each other to give mixed species. A conformationally restricted diol derived from sucrose affords an eight-membered cyclic dioxytriphenylphosphorane. ³¹P And ¹³C n.m.r. data for these phosphoranes are reported.