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Paper | Regular issue | Vol 94, No. 2, 2017, pp.255-275
Published online, 30th January, 2017
DOI: 10.3987/COM-16-13583
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

Isamu Shiina* and Takayuki Tonoi

*Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan


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.