Synthesis of organochalcogens stabilized by intramolecular nonbonded interactions of sterically unhindered 2-phenyl-2-oxazoline

Abstract

The synthesis and characterization of low-valent organoselenium and -sulfur compounds incorporating sterically unhindered 2-phenyl-2-oxazoline are described. Organylselenenyl halides, RSeX (X = Cl, Br, I) were prepared from diselenide and the benzyl selenide derivative was synthesized by the reaction of in situ generated lithium arylselenolate, OxSe(-)Li(+) (Ox = 2-phenyl-2-oxazoline) with benzyl chloride. These compounds in general show strong Se...N intramolecular interactions as compared with the substituted oxazoline analogues. Bis[2-(2-oxazolinylphenyl)]disulfide and [2-(2-oxazolinyl)phenyl] benzyl sulfide were synthesized by the ortho-lithiation method and characterized by H-1 and C-13 NMR spectroscopy. The S...N intramolecular interactions were confirmed by single crystal X-ray crystallography.