EXPEDITIOUS SYNTHESIS OF CARBOXYLIC ESTERS AND HIGH-YIELDING MACROLACTONES USING TRIFLUOROMETHYL-SUBSTITUTED BENZOIC ANHYDRIDES WITH 4-(DIMETHYLAMINO)PYRIDINE: AN EVALUATION OF THE REACTIVITIES OF AROMATIC ACID ANHYDRIDES AS DEHYDRATION REAGENTS COMPARED WITH 2-METHYL-6-NITROBENZOIC ANHYDRIDE

摘要

Trifluoromethyl-substituted benzoic anhydrides as structural congeners of 2-methyl-6-nitrobenzoic anhydride (MNBA) were prepared and investigated for comparative reactivity in the synthesis of carboxylic esters and macrolactones. 2-Fluoro-6-(trifluoromethyl)benzoic anhydride (FTFBA) was found to be a promising dehydrating agent in the presence of 4-(dimethylamino)pyridine (DMAP), and was successfully employed in the synthesis of threo-aleuritic acid lactone in good yield with high chemoselectivity.