β Scribed by Peta J. Harvey; Mark von Itzstein; Ian D. Jenkins
No coin nor oath required. For personal study only.
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 pnitrobenzoic 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 lormation in the latter case.
π SIMILAR VOLUMES
The Mitsunobu reaction Β± the nucleophilic substitution of an alcoholic hydroxyl group mediated by the redox system trialkylphosphine/dialkyl azodicarobxylate Β± is widely used in the chemistry of biologically active compounds. The paper deals with applications of the Mitsunobu reaction in amino acid