MILD ESTERIFICATION AND TRANSESTERIFICATION OF CARBOXYLIC-ACIDS CATALYZED BY TETRACYANOETHYLENE AND DICYANOKETENE DIMETHYL ACETAL

A pi-acid tetracyanoethylene (TCNE) and its derivative dicyanoketene d imethyl acetal (DCKDMA) were found to catalyze esterification of lauri c acid with various types of alcohols. This method was successfully ap plied to methyl esterification of a variety of carboxylic acids includ ing aromatic, alpha,beta-unsaturated, alpha-hydroxy, and N-Cbz and N-B oc-protected alpha-amino acids without racemization at the range from room temperature to 60 degrees C. TCNE was also found to operate as a catalyst in transesterification reaction of methyl laurate.