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Synthesis of new 1,3-oxaphosphorinanium salts. Stereochemistry of hydroxide-induced displacement of methoxide ion.
López-Cortina, Susana; Basiulis, Danute I; Marsi, Kenneth L; Muñoz-Hernández, Miguel Angel; Ordoñez, Mario; Fernández-Zertuche, Mario.
Afiliación
  • López-Cortina S; Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Col. Chamilpa, 62210, Cuernavaca, Morelos, México.
J Org Chem ; 70(19): 7473-8, 2005 Sep 16.
Article en En | MEDLINE | ID: mdl-16149773
[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.
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Banco de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2005 Tipo del documento: Article
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Banco de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2005 Tipo del documento: Article