Computational assessment of non-heteroatom-stabilized carbene complexes reactivity: Formation of oxazine derivatives

  1. Funes-Ardoiz, I. 1
  2. Sampedro, D. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Journal of Organic Chemistry

ISSN: 0022-3263

Año de publicación: 2014

Volumen: 79

Número: 23

Páginas: 11824-11828

Tipo: Artículo

DOI: 10.1021/JO5023684 SCOPUS: 2-s2.0-84916631366 WoS: WOS:000346038300057 GOOGLE SCHOLAR

Otras publicaciones en: Journal of Organic Chemistry

Resumen

A complete DFT-level mechanism elucidation of the two-step reaction of non-heteroatom-stabilized carbenes with imines, followed by addition of alkynes to yield oxazine derivatives, is presented. These compounds show different reactivity than the equivalent Fischer carbene complexes. A rationale of the experimental outcome is presented together with some suggestion for increasing the scope of the reaction, with special attention to the solvent effects in the regioselectivity.