López-Cortina Susana, Basiulis Danute I, Marsi Kenneth L, Muñoz-Hernández Miguel Angel, Ordoñez Mario, Fernández-Zertuche Mario
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Col. Chamilpa, 62210, Cuernavaca, Morelos, México.
J Org Chem. 2005 Sep 16;70(19):7473-8. doi: 10.1021/jo050901w.
[reaction: see text] The synthesis of pure cis- and trans-3-methoxy-2,2,6-trimethyl-3-phenyl-1,3-oxaphosphorinanium tetrafluoroborate salts 3a and 3b, respectively, molecules designed to evaluate the effect of oxygen on the steric course of base-induced nucleophilic displacement of the methoxy group at phosphorus, was accomplished. It was found that these isomeric salts react with aqueous sodium hydroxide to produce the corresponding phosphine oxides 7a and 7b with complete retention of configuration at phosphorus.
