Tetrahedron p. 3933 - 3942 (1997)
Update date:2022-08-11
Topics:
Harvey, Peta J.
Von Itzstein, Mark
Jenkins, Ian D.
Treatment of benzoic acid with triphenylphosphine and diisopropyl azodicarboxylate in THF or acetonitrile, results in the formation of benzoic anhydride. A significant solvent effect was observed for this reaction. Anhydride formation did not occur however with the more acidic p-nitrobenzoic acid. Relative rate and competition experiments suggest that the improved yields observed when p-nitrobenzoic acid is used instead of benzoic acid in the Mitsunobu esterification reaction are due to competitive anhydride formation in the latter case.
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