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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Preparation of 13C4-6-methyl anthranilic ester via a Diels-Alder-type process. an experimental and theoretical study
J Lorenzo Alonso-Gómez1, Yolanda Pazos, Armando Navarro-Vázquez
1Departamento de Química Orgánica, Universidade de Vigo, 36310 Vigo, Spain.
Abstract:
Buta-2,3-dienoate reacts with vinyl ketenimine to give the corresponding substituted aniline through a Diels-Alder cycloaddition. Besides the expected Diels-Alder adduct 3a, the aniline 3b was also obtained in a ratio of 91:9. The observed (13)C exchange is explained on the basis of a reversible [2 + 2] cycloaddition competing with the [4 + 2] process. This is supported by B3LYP DFT computations, as a stepwise pathway lies very close in energy to the [4 + 2] concerted one. [reaction: see text]
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