The thiosulfinyl group serves as a stereogenic center and shows diamagnetic anisotropy similar to that of the sulfinyl group

Journal of the American Chemical Society
Sanae TanakaJuzo Nakayama

Abstract

The pseudotetrahedral geometry of the thiosulfinyl group (>S=S) in the thionosulfite which was prepared by treatment of cis-3,4-di-tert-butylthiolane-3,4-diol with 1,1'-thiobisbenzimidazole is stable enough to allow the isolation of two diastereomers. X-ray crystallographic analysis revealed that the configuration of the >S=S group of the major diastereomer (45% isolated yield) is syn to the thiolane ring, while that of the minor diastereomer (10% isolated yield) is anti to the thiolane ring. 1H NMR spectrum analysis clarified that the shielding and deshielding zones of the >S=S group are similar to those of the >S=O group. Chemical properties of the >S=S group toward thermolysis, hydrolysis, and oxidation were clarified. The absorptions or bands in the UV/vis, IR, and Raman spectra, which originate from the >S=S group, were assigned on the basis of the B3LYP/6-31G* level calculations.

Citations

Apr 9, 2014·Chemistry : a European Journal·Marie BetouRichard S Grainger
Jul 28, 2019·Physical Chemistry Chemical Physics : PCCP·Steffen MerzJosef Granwehr
Jul 16, 2005·The Journal of Organic Chemistry·Eli Zysman-Colman, David N Harpp
Apr 20, 2012·Organic Letters·Richard S GraingerSimon J Coles
Jun 13, 2018·The Journal of Physical Chemistry. a·Sebastian Jung, Joachim Podlech
Jan 5, 2006·Journal of the American Chemical Society·Eli Zysman-ColmanDavid N Harpp
Apr 7, 2007·The Journal of Organic Chemistry·Nicolas Eghbali, David N Harpp
Apr 23, 2005·The Journal of Organic Chemistry·María Elena González-NúñezFernando López Ortiz
Apr 28, 2006·The Journal of Physical Chemistry. a·Xiaoqing ZengDianxun Wang

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