82135-88-4Relevant articles and documents
Reaction of a cyclic oxosulfonium ylide with acetates of the Baylis-Hillman adducts: Tandem Michael - Intramolecular Corey-Chaykovsky reactions
Akiyama, Hitoshi,Fujimoto, Tetsuya,Ohshima, Katsuyoshi,Hoshino, Kenji,Yamamoto, Iwao,Iriye, Ryozo
, p. 427 - 430 (2008/02/12)
(equation presented) The reaction of the five-membered cyclic oxosulfonium ylide 2 with α-methylene-β-acetoxy ketones in the presence of two equimolar amounts of base afforded the cycloheptene oxide derivatives with stereoselectivity in 19-74% yield via a
One-Electron Chemical Reductions of Phenylalkylsulfonium Salts
Beak, Peter,Sullivan, Thomas A.
, p. 4450 - 4457 (2007/10/02)
Twenty-two arylalkylsulfonium salts have been reduced with potassium in graphite in tetrahydrofuran and the sulfide products identified.Two trialkylsulfonium salts did not reduce under these conditions.Comparison of the sulfides from a series of monophenylalkylsulfonium salts reveals a leaving-group propensity of benzyl > secondary > primary > methyl > phenyl in a ratio of 28:(6.0 +/- 0.3):1.0:(0.53 +/- 0.09): 0.05.The cleavage ratio is shown to be independent of the electron source and the homogeneity of heterogeneity of the reaction in two cases.Multiplicative transitivity of the above ratios is not observed, although the same qualitative order is found for other comparisons.These results are interpreted in terms of the initial formation of a ?-ligand radical anion sulfonium cation, which undergoes cleavage to a carbon radical and a sulfide.This appears to be the first evidence for this type of structure in a sulfur system.Leaving-group propensities different from the above order are observed in reductions of diphenylsulfonium and benzo-fused sulfonium salts, and rationales are offered.The intermediates in these reactions appear to be different from those involved in radical additions to, or displacements on, sulfur.