Stereospecific Replacement of the Boranato Group of Phosphine–Boranes by Oxygen or Sulfur. Synthesis of Optically Active, P-Chiral Phosphine Oxides, Phosphine Sulfides, Phosphinates, and Phosphinothioates

Article type: Research Article

Authors: Imamoto, Tsuneo | Hirose, Koutaro | Amano, Hiroshi | Seki, Hiroko

Affiliations: Department of Chemistry, Faculty of Science, Chiba University, Inage, Chiba 263, Japan | Chemical Analysis Center, Chiba University, Inage, Chiba 263, Japan

Note: [] Corresponding Author

Abstract: Optically active, P-chiral phosphine–boranes were oxidized by m-chloroperbenzoic acid to give phosphine oxides or phosphinates with almost complete retention of configuration. The oxidation of the same phosphine–boranes with iodine in the presence of water occurred with inversion of configuration in good to high stereospecificity. The reaction of the phosphine-boranes with sulfur in the presence of N-methylmorpholine proceeded with net retention of configration to afford optically active phosphine sulfides or phosphinothioates.

DOI: 10.1080/13583149612331338627

Journal: Main Group Chemistry, vol. 1, no. 3, pp. 331-338, 1996