Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study

  1. Barluenga, J. 2
  2. González, J.M. 2
  3. Llorente, I. 2
  4. Campos, P.J. 1
  5. Rodríguez, M.A. 1
  6. Thiel, W. 3
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Universidad de Oviedo
    info

    Universidad de Oviedo

    Oviedo, España

    ROR https://ror.org/006gksa02

  3. 3 University of Zurich
    info

    University of Zurich

    Zúrich, Suiza

    ROR https://ror.org/02crff812

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Revista:
Journal of Organometallic Chemistry

ISSN: 0022-328X

Año de publicación: 1997

Volumen: 548

Número: 2

Páginas: 185-189

Tipo: Artículo

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DOI: 10.1016/S0022-328X(97)00403-8 SCOPUS: 2-s2.0-0031564350 WoS: WOS:000071575400010 GOOGLE SCHOLAR

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Resumen

Ab initio calculations with complete geometry optimization are reported for monomeric Z- and E-2-methoxy-1-iodo-1-lithio-2-phenyl-1-alkenes. All the stationary points are true local minima on the energy surfaces. The structural data of the lithioalkenes show clear-cut evidence for the Li-Phenyl interaction in Z-isomer and the Li-O chelation in E-isomer in gas-phase. Based on the ab initio energies, Li-Phenyl interaction should be less relevant than Li,O chelation. Both effects are absent when coordination by solvent (water) is accounted. Inclusion of solvation by solvent continuum model (IPCM) seems essential to rationalize the experimental results. © 1997 Elsevier Science S.A.