82937-29-9Relevant 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.
Stereoselective Addition Reaction of Allylic Sulfides to Acetylenic Esters: E/Z Stereochemical Variations by Lewis Acid
Hayakawa, Kenji,Kamikawaji, Yoshimasa,Wakita, Akemi,Kanematsu, Ken
, p. 1985 - 1989 (2007/10/02)
The Lewis acid catalyzed addition reactions of allylic sulfides to methyl propiolate (MP) and dimethyl acetylenedicarboxylate (DMAD) have been investigated.The stereochemical outcome is considerably influenced by the Lewis acid.While the AlCl3-catalyzed r
ALUMINIUM-CHLORIDE CATALYZED REACTION OF ALLYLIC SULFIDES WITH METHYL PROPIOLATE: A NOVEL ADDITION REACTION VIA AN IONIC SIGMATROPIC REARRANGEMENT
Hayakawa, Kenji,Kamikawaji, Yoshimasa,Kanematsu, Ken
, p. 2171 - 2174 (2007/10/02)
The aluminium-chloride catalyzed reaction of allylic sulfides with methyl propiolate resulted in the clean formation of novel 1:1 adducts via ionic sigmatropic rearrangements.
