Synthesis of organochalcogens stabilized by intramolecular non-bonded 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 ¹H and ¹³C NMR spectroscopy. The S···N intramolecular interactions were confirmed by single crystal X-ray crystallography.