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

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 inte...

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Detalles Bibliográficos
Autores: Barluenga, J. [0000-0002-6474-7782], González, J.M. [0000-0002-7869-9873], Llorente, I., Campos, P.J. [0000-0002-8917-0318], Rodríguez, M.A. [0000-0003-0123-9905], Thiel, W. [0000-0001-6780-0350]
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:1997
País:España
Institución:Universidad de La Rioja (UR)
Repositorio:RIUR. Repositorio Institucional de la Universidad de La Rioja
OAI Identifier:oai:portal.dialnet.es:doc/5bbc68cbb750603269e80fac
Acceso en línea:https://investigacion.unirioja.es/documentos/5bbc68cbb750603269e80fac
Access Level:acceso abierto
Descripción
Sumario: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.

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