Bulletin of the Chemical Society of Japan p. 3469 - 3482 (1995)
Update date:2022-08-02
Topics:
Fukushima, Kazuaki
Ibata, Toshikazu
The Rh2(OAc)4-catalyzed reactions of α-diazocarbonyl compounds in nitrile in the presence of dimethyl acetylenedicarboxylate (DMAD) gave oxazole and pyrrole derivatives.The formation of the oxazole derivatives is explained in terms of the 1,5-cyclization of an acyl-substituted nitrile ylide intermediate, and the formation of the pyrrole derivatives is explained by the 1,3-dipolar cycloaddition of the same intermediate with DMAD.The regiochemistry of the cycloaddition of the acyl-substituted nitrile ylide with methyl propiolate showed that the contribution of an allenyl-type resonance structure plays an important role in the acyl-substituted nitrile ylide reaction.
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Doi:10.1021/jo01298a034
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