86409-96-3Relevant articles and documents
Sulfonylation and Phosphinylation of Olefinic Compounds with Radical Species Generated by the Oxidation of Sodium Sulfinates and Diphenylphosphine Oxide
Mochizuki, Takashi,Hayakawa, Satoshi,Narasaka, Koichi
, p. 2317 - 2325 (2007/10/03)
Sodium arenesulfinates are oxidized with manganese(III) 2-pyridinecarboxylate or ammonium cerium(IV) nitrates to generate sulfonyl radicals, which add to olefinic compounds to afford sulfonylated products in good yield. When 1-vinyl cyclic alcohols are used as sulfonyl radical acceptors, sulfonylation proceeds with ring-enlargement. Diphenylphosphinyl radical can also be generated by treating diphenylphosphine oxide with manganese(III) 2-pyridinecarboxylate and reacts with olefinic compounds, giving phosphinylated products.
Selenosulfonation of Acetylenes: Preparation of Novel β-(Phenylseleno)vinyl Sulfones and Their Conversion to Acetylenic and β-Functionalized Sulfones
Back, Thomas G.,Collins, Scott,Kerr, Russell G.
, p. 3077 - 3084 (2007/10/02)
The 1,2-additions of Se-phenyl p-tolueneselenosulfonate (1) to acetylenes under mild conditions afford β-(phenylseleno)vinyl sulfones 3, generally in high yields.The reaction is highly regioselective (anti-Markovnikov) and stereoselective (anti) and proceeds via a free-radical chain mechanism initiated by the thermolysis of the selenosulfonate.The oxidation of β-(phenylseleno)vinyl sulfones with m-chloroperbenzoic acid generates the corresponding selenoxides 4, which undergo syn or base-catalyzed elimination to furnish acetylenic sulfones 5.Base-catalyzed alcoholyses of selenoxides 4 in methanol or ethylene glycol produce β-keto sulfone ketals 8 or 10, respectively.Free β-keto sulfones 11 are formed by the acid-catalyzed hydrolysis of the corresponding β-(phenylseleno)vinyl sulfones 3.