Revised mechanism and improved methodology for the Perkin condensation. Resuscitation of the mechanism involving benzal acetate and the improbability of the enolate of acetic anhydride |
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Authors: | Sosale Chandrasekhar Phaneendrasai Karri |
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Institution: | Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India |
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Abstract: | The Perkin condensation most likely occurs via the initial formation of a gem-diacetate from the aromatic aldehyde and acetic anhydride reactants. The key reactive nucleophile appears to be the enolate of the gem-diacetate rather than of acetic anhydride. The diacetate from PhCHO may be converted to cinnamic acid under a variety of (relatively) mild basic conditions. |
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Keywords: | Acetic anhydride gem-Diacetate Cinnamic acid Enolate Perkin condensation |
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