Novel Synthetic Reactions Using 1-Fluoro-2,4,6-trinitrobenzene. An Efficient Direct Esterification Method

摘要

Synthetic utility of 1-fluoro-2,4,6-trinitrobenzene (FTNB) as a condensing agent was investigated. The use of FTNB and DMAP was found to be very effective for direct esterification of carboxylic acids with alcohols or thiols. However, this system was not very effective for macrolactonization. Reaction of 2,4,6-trinitrophenyl esters with several nucleophiles was investigated briefly. Plausible reaction mechanisms of esterification are presented. It seems that the reaction proceeds via the intermediacy of 2,4,6-trinitrophenyl esters by initial formation of 2`,4`,6`-trinitrophenyl-4-dimethylaminopyridinium salt from which the trinitrophenyl group is transferred to the carboxylic acid.