7110-00-1Relevant academic research and scientific papers
Nucleophilic attack of 2-sulfinyl acrylates: A mild and general approach to sulfenic acid anions
Singh, Suneel P.,O'Donnell, Jennifer S.,Schwan, Adrian L.
supporting information; experimental part, p. 1712 - 1717 (2010/07/04)
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.
β-Sulfinyl acrylate esters as a convenient source of alkane- and arenesulfenate anions
O'Donnell, Jennifer S.,Schwan, Adrian L.
, p. 6293 - 6296 (2007/10/03)
Methyl acrylate esters bearing alkane- and arenesulfinyl units on the 2-carbon liberate sulfenate anions upon nucleophilic attack. The sulfenates are readily captured through sulfur alkylation. When a sulfenate derived from R-cysteine is generated, diastereoselective benzylation is observed.
