N,N′-Oxalyl-Di-Imidazolide - A New Reagent for the Synthesis of Symmetrical Organic Oxalates

Abstract

As part of our program to investigate the behavior of pentadianyl radicals, we wished co prepare bis(δ^1,1′ -dicyclohexenyl carbinyl) oxalate (I) and study Its thermal decomposition. Application of the usual methods of oxalate synthesis toward the preparation of I resulted in low or zero yields, those methods involve reaction conditions whereby an acid is used directly in the reaction¹ or is generated during the reaction as a by product². Since we have found I to be sensitive to even trace amounts of acids³, we sought to develop an alternate approach to oxalate synthesis that would avoid adds at all stages.