Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Novel Synthetic Reactions Using 1-Fluoro-2, 4, 6-trinitrobenzene. An Efficient Direct Esterification Method

  • Kim Sunggak (Contribution from Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Ahn Kyo Han (Contribution from Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Yang Sungbong (Department of Industrial Chemistry, Ulsan Institute of Technology)
  • Published : 1982.06.30
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Abstract

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.

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