Synthesis and characterization of 3,5-lutidinyl chalcogen and -dichalcogen compounds: X-ray crystal structure of bis(3,5-dimethyl-2-pyridyl) diselenide and 2,6-bis(selenomethyl)-3,5-lutidine

The synthesis of 3,5-lutidinyl chalcogen and -dichalcogen compounds has been described by a method involving selective mono- and dilithiation of 3,5-lutidine (1) ring. The selective mono- and dilithiation of 1 has been achieved by reacting BF3-complexed 3,5-lutidine (2) with 1 and 2 equiv of LTMP/LDA respectively. The subsequent insertion of elemental selenium followed by aerial oxidation or quenching with iodomethane leads to the formation of bis(3,5-dimethyl-2-pyridyl) diselenide (5) and 2,6-bis(selenomethyl)-3,5-lutidine (7) respectively. In addition, sequential incorporation of sulfur and selenium atom in the same lutidine ring has been reported for the first time. Single-crystal X-ray studies of (5), having a rare C–Se–Se–C torsion angle of 180°(4), and (7) have also been reported.

Graphical abstractThe synthesis of 3,5-lutidinyl chalcogen and -dichalcogen compounds has been described by a method involving selective mono- and dilithiation of 3,5-lutidine (1) ring. The selective mono- and dilithiation of 1 has been achieved by reacting BF3-complexed 3,5-lutidine (2) with 1 and 2 equiv of LTMP/LDA respectively.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights►Synthesis of 3,5-lutidyl monochalcogen and -dichalcogen compounds. ►Introduction of two same or two different chalcogen atoms in the same lutidine ring. ►A rare C–Se–Se–C torsion angle of 180° in disubstituted dipyridyl diselenide.