Oxidative Addition of Diorgano Disulfides to Distannyne [{2,6‐(Me₂NCH₂)₂C₆H₃}Sn]₂

Abstract

Reactivity of [{2,6‐(Me2NCH2)2C6H3}Sn]2 (1) towards functionalized diorganodisulfides R2S2 as oxidizing agents was studied. The reactions provided organotin(II) thio derivatives {2,6‐(Me2NCH2)2C6H3}Sn(S2CNMe2) (2), {2,6‐(Me2NCH2)2C6H3}Sn (SC6H4‐2‐NH2) (3) and {2,6‐(Me2NCH2)2C6H3}Sn(SC5H4N) (4). The 119Sn NMR spectroscopic data of 2–4 suggest different electronic saturation of the tin(II) atoms in 2–4, which caused redox stability of 2 and easy oxidation of 3 and 4. The treatment of the latter compounds with diorgano disulfides R2S2 yielded organotin(IV) thio derivatives {2,6‐(Me2NCH2)2C6H3}Sn(SC6H4‐2‐NH2)3 (5) and {2,6‐(Me2NCH2)2C6H3}Sn(SC5H4N)3 (6). In addition, oxidation of 3 and 4 with the radical TEMPO (2,2,6,6‐tetramethylpiperidin‐1‐oxyl) provided organotin(IV) hydroxide [{2,6‐(Me2NCH2)2C6H3}Sn(SC6H4‐2‐NH)(μ‐OH)]2 (7) and organotin(IV) oxide [{2,6‐(Me2NCH2)2C6H3}Sn(SC5H4N)(μ‐O)]3 (8). All prepared compounds 2–8 were characterized by using multinuclear NMR spectroscopy, and the molecular structures of 2, 4, 7 and 8 were determined by using X‐ray diffraction. Compounds 2–4 were also characterized by cyclic voltammetry.

SnS and SnS2thin films deposited using a spin‐coating technique from intramolecularly coordinated organotin sulfides

“…Compounds 1 , 2 , 3 were prepared and characterized according to the literature . Their stability in various solvents was tested further.…”

“…All moisture‐ and air‐sensitive reactions were carried out in an argon atmosphere using standard Schlenk techniques. Compounds 1 , 2 , 3 were prepared and characterized using 1 H NMR and 119 Sn NMR spectroscopy according to the literature …”

“…Both compounds were dissolved in dichloromethane, toluene or propylene amine, stirred for 1 h and the volatile material was evaporated. The remaining solid material was dissolved in C 6 D 6 ( 2 ) or CDCl 3 ( 3 ) and characterized as non‐decomposed complexes 2 and 3 using NMR spectroscopy . Toluene, dichloromethane and propylene amine saturated solutions of 2 and 3 were prepared and used for the spin‐coating experiments to synthesize thin films of SnS and SnS 2 .…”

The Role of Monoanionic Aryl Pincer Ligands in the Stabilization of Group 14 Metallylenes

“…[42] Derivative 44 in reaction with diorgano disulfides formed the corresponding organotin(II) thio derivatives. [44] The redox potential of the tin atom in the diorganodistannyne L I SnSnL I [L I = 2,6-(R2NCH2)2C6H3, R = Me], [45] as well as the reduction ability of these type of distannynes were also studied. [46] The coordination ability of chlorostannylene 27 was tested towards different transition metal complexes, as show in Scheme 10.…”