| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5289267 | Tetrahedron Letters | 2006 | 4 Pages |
Abstract
Azlactone anions-the key intermediates in the classical Erlenmeyer synthesis of amino acids-apparently possess aromatic stabilization, as indicated by the relative rate of base catalyzed deuterium exchange in the following analogs: 1-methyl-2-phenyl-5(4H)-imidazolone > 2-phenyl-5(4H)-oxazolone (azlactone) > 3,3-dimethyl-2-phenyl-4(3H)-pyrrolone. This is paralleled by the relative rate of condensation of these compounds with hexadeuteroacetone. Reported pKa data also suggest that the azlactone products of the Erlenmeyer synthesis are analogs of the fulvenes.
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Authors
Sosale Chandrasekhar, Phaneendrasai Karri,