Synthesis and characterization of 2,6-Dipp(2)-H(3)C(6)SnSnC(6)H(3)-2,6-Dipp(2) (Dipp = C(6)H(3)-2,6-Pr(i)(2)): a tin analogue of an alkyne.

The reaction of Sn(Cl)C(6)H(3)-2,6-Dipp(2) (Dipp = C(6)H(3)-2,6-Pr(i)()(2)) with a stoichiometric amount of potassium in benzene affords 2,6-Pr(i)()(2)-H(3)C(6)SnSnC(6)H(3)-2,6-Pr(i)()(2) (1) as dark blue-green crystals. The compound 1 is a tin analogue of an alkyne. It was characterized by (1)H and (13)C NMR and UV-vis spectroscopy, cyclic voltammetry, combustion analysis and X-ray crystallography. The structural data show that 1 has a trans-bent, planar C(ipso)SnSnC(ipso) skeleton with a Sn-Sn bond distance of 2.6675(4) A and a Sn-Sn-C angle of 125.24(7) degrees. The Sn-Sn distance, which is ca. 0.15 A shorter than a conventional Sn-Sn single bond, and the trans-bent structure indicate the presence Sn-Sn multiple bond character unlike the related singly bonded ArPbPbAr species.