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Sulfur-containing Compounds

  • Chapter
Free Radicals in Organic Synthesis

Part of the book series: Reactivity and Structure: Concepts in Organic Chemistry ((REACTIVITY,volume 7))

Abstract

The weak sulfur-sulfur bond in elemental sulfur allows carbon-centred radicals and thiyl radicals to effect Sh2 reactions at such sulfur atoms leading to the formation of poly sulfides. For example [1],

$$ Me_2 \dot CCN + S_8 \to Me_2 (CN)CS_n C(CN)Me_2 $$

and [2]

$$ MeSSMe\xrightarrow{{120^\circ C}}2MeS \cdot $$
$$ MeS \cdot + S_8 \xrightarrow{{MeS \cdot /MeSSMe}}MeS_n Me $$

There are comprehensive accounts of these and other analogous reactions [3–5]. Polysul-fides are reduced with lithium aluminium hydride to thiols, which offers a route to thiols of limited preparative value [6]. Sulfur monochloride reacts with alkanes via displacement reactions at sulfur affording a mixture of disulfides, polysulfides, and alkyl chlorides [6].

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Authors and Affiliations

  1. Department of Chemistry, University of London King’s College, Strand London, WC2R 2LS, England

    David Ian Davies

  2. Department of Chemistry, Institute of Science and Technology, University of Manchester, P.O. Box 88, Manchester, M60 1QD, England

    Maxwell James Parrott

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© 1978 Springer-Verlag Berlin Heidelberg

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Davies, D.I., Parrott, M.J. (1978). Sulfur-containing Compounds. In: Free Radicals in Organic Synthesis. Reactivity and Structure: Concepts in Organic Chemistry, vol 7. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-66922-4_10

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  • DOI: https://doi.org/10.1007/978-3-642-66922-4_10

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-66924-8

  • Online ISBN: 978-3-642-66922-4

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