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New Aspects of Hypervalent Organosulfur Compounds

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Organosulfur Chemistry II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 205))

Abstract

The chemistry of sulfuranes has developed greatly and has attracted attention of many organic chemists over the past two decades. This work describes the historical background, the development, and the synthesis of sulfuranes and persulfuranes. The concept of hypervalent bonding was introduced by Rundle and Musher; before the pioneering work of Martin and Kapovits on the preparation of sulfuranes, these compounds were considered only to be unstable intermediates or simple transition states in nucleophilic substitution reactions at sulfur atoms. There are many reports of unstable sulfuranes being formed during the substitution reactions of dicoordinated, tricoordinated and even tetracoordinated sulfur atoms with various nucleophiles. However, neither direct nor spectroscopic evidence for the formation of sulfuranes had been reported until in the 1970s, when Martin found methods for syntheses of the stable sulfuranes. Ligand exchange and coupling reactions are typical reactions of tricoordinated sulfur compounds with nucleophiles, and are considered to be diagnostic for the formation of sulfuranes. According to Martin’s definition, stable sulfuranes should contain electronegative substituents to provide the hypervalent bonds. However, quite recently, sulfuranes bearing only carbon substituents have been synthesized. This work describes both the intermediary formation of sulfuranes and stable isolable sulfuranes, together with their chemical behaviors.

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  1. Tsukuba Advanced Research Alliance Center, Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki, 305, Japan

    Naomichi Furukawa & Soichi Sato

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  1. Naomichi Furukawa
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  2. Soichi Sato
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  1. Department of Chemistry, Loughborough University, LEU 3TU, Leicestershire, UK

    Philip C. B. Page

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Furukawa, N., Sato, S. (1999). New Aspects of Hypervalent Organosulfur Compounds. In: Page, P.C.B. (eds) Organosulfur Chemistry II. Topics in Current Chemistry, vol 205. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48986-X_2

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