STEREOCHEMISTRY OF ORGANOPHOSPHORUS CYCLIC COMPOUNDS-XV SYNTHESIS OF TETRAMETHYLAMMONIUM SALT OF 2-OXO-2-THIO-1,3,2-OXAZAPHOSPHORINAN AND ITS CRYSTAL AND MOLECULAR STRUCTURES

Article abstract of DOI:10.1016/0040-4020(82)85165-X

2-Hydroxy-1,3,2-oxazaphosphorinan-2-thione(5) was prepared by alkaline hydrolysis of 2-chloro-1,3,2-oxazaphosphorinan-2-thione(6).Treatment of the latter with sodium methoxide afforded the 2-methoxy-derivative 7 from which the tetramethylammonium salt of the thioacid 5 was obtained by the action of trimethylamine.The structure of this salt has been determined by the direct method and refined by least-squares to R=0.0734, a=12.303(4), b=9.041(3), c=10.419(2)Angstroem, space group P2₁2₁2₁.The 2-oxo-2-thio-1,3,2-oxazaphosphorinanyl anion is in the chair form with the exocyclic S and O atoms in an axial and equatorial position, respe ctively.An intermolecular H-bond between S and the endo-cyclic N atom is present in the solid-state structure.