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Issue 7, 2010
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Nucleophilic attack of 2-sulfinyl acrylates: A mild and general approach to sulfenic acid anions

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Abstract

An increasing number of reactions of sulfenic acid anions are being demonstrated in the literature. As such, mild, general and reliable means for the generation of sulfenates are due. In the current paper, an addition/elimination of 2-sulfinyl acrylates using various nucleophiles is demonstrated and evaluated as a protocol for alkane- and arenesulfenate generation. Cyclohexanethiolate, methoxide and n-butyllithum each exhibit some merit for the reaction, and the thiolate is established as a mild, selective and effective reagent to release sulfenates from 2-sulfinyl acrylates. The stereospecificity of the addition/elimination of each nucleophile is recognized, and an explanation for the specificity is offered for thiolate and methoxide.

Graphical abstract: Nucleophilic attack of 2-sulfinyl acrylates: A mild and general approach to sulfenic acid anions

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Publication details

The article was received on 20 Aug 2009, accepted on 09 Jan 2010 and first published on 10 Feb 2010


Article type: Paper
DOI: 10.1039/B917217C
Citation: Org. Biomol. Chem., 2010,8, 1712-1717
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    Nucleophilic attack of 2-sulfinyl acrylates: A mild and general approach to sulfenic acid anions

    S. P. Singh, J. S. O'Donnell and A. L. Schwan, Org. Biomol. Chem., 2010, 8, 1712
    DOI: 10.1039/B917217C

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