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Structure and Properties of a Sulfur(IV)[BOND]Sulfur(II)-Bond Compound: Reversible Conversion of a Sulfur-Substituted Organosulfurane into a Thiol

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  • We thank Tosoh Finechem Corp., Shin-etsu Chemical Co. Ltd., and Central Glass Co., Ltd. for gifts of alkyl lithium, silicon reagents, and fluorine compounds, respectively. This work was partially supported by the Global COE Program for Chemistry Innovation and for Scientific Researches from the Ministry of Education, Culture, Sports, Science and Technology (Japan) and the Japan Society for the Promotion of Science.

Abstract

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A highly polar hypervalent SIV[BOND]SII bond was formed in the synthesis of a sulfur-substituted sulfurane (see scheme), which was crystallographically characterized. Reduction of the 1,2-dithietane gives the corresponding thiol, and reoxidation gives the sulfurane by S[BOND]S bond reformation. Thermal decomposition leads to a cyclic sulfenate and a thiirane.

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