Reactivity of 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE) with O-nucleophiles generated by potassium tert-butoxide

Pellizzaro, Leonardo; Cabianca, Elena; Tatibouët, Arnaud; Padovan, Pierluigi; Fabris, Fabrizio; Rollin, Patrick; Lucchi, Ottorino De

doi:10.1016/j.tetlet.2007.03.125

Cited by 3 publications

(1 citation statement)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…De Lucchi and coworkers have suggested that electron-deficient compounds with alkene chemical shifts in the order of 138-140 ppm favour addition/elimination over elimination/addition. 25 The mechanism for the reactions with n-BuLi is less certain. Unsaturated ester 6 and lesser amounts of 7 were consistently observed as part of the reaction profiles of the reaction with n-BuLi.…”

Section: Resultsmentioning

confidence: 99%

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

2010

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

confidence: 99%