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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 3, Number 2
February 20, 1982 

Novel Synthetic Reactions Using 1-Fluoro-2,4,6-trinitrobenzene. An Efficient Direct Esterification Method
Sunggak Kim, Kyo Han Ahn, Sungbong Yang
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.
70 - 76
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