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The Chemistry of the Thiosulfinyl Group: Preparation, Structure, and Spectroscopic and Chemical Properties of Cyclic Thionosulfites by Juzo Nakayama; Sanae Yoshida (nee Tanaka); Yoshiaki Sugihara; Akira Sakamoto is a Chemistry article available to read on EtoBox.

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## Abstract Treatment of the tetrahydrothiophene‐3,4‐diol **5** with 1,1′‐thiobis‐(1__H__‐benzimidazole) (**6**) furnished two diastereoisomers of the novel cyclic thionosulfite **4** with different configurations at the pseudo‐tetrahedral center of the thiosulfinyl (SS) group. The configuration of the SS group of the major diastereoisomer (isolated in 45% yield) was established to be __syn__ to the thiolane ring, as determined by X‐ray crystallographic analysis, while that of the minor diastereoisomer (isolated in 10% yield) was __anti.__ ^1^H‐NMR Spectroscopic analysis clarified that the shielding and deshielding zones of the SS group are similar to those of the well‐documented SO group. Characteristic absorptions of the SS group in the IR, __Raman__, and UV/VIS spectra were assigned on the basis of calculations at the B3LYP/6‐31G\* level. The reactivity of the SS group toward thermolysis, hydrolysis, and oxidation was examined. The SS group is more resistant toward oxidation than the divalent sulfide S‐atom, but is oxidatively converted to the SO group.

Who reads The Chemistry of the Thiosulfinyl Group: Preparation, Structure, and Spectroscopic and Chemical Properties of Cyclic Thionosulfites?

Author

Juzo Nakayama; Sanae Yoshida (nee Tanaka); Yoshiaki Sugihara; Akira Sakamoto

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)

Published

2005

Language

EN

Field

Chemistry (Physical Sciences)