Synthesis of new 1,3-oxaphosphorinanium salts. Stereochemistry of hydroxide-induced displacement of methoxide ion.
[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.
López-Cortina
Susana
S
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Col. Chamilpa, 62210, Cuernavaca, Morelos, México.
Basiulis
Danute I
DI
Marsi
Kenneth L
KL
Muñoz-Hernández
Miguel Angel
MA
Ordoñez
Mario
M
Fernández-Zertuche
Mario
M