Mercury-Photosensitized Sulfination, Hydrosulfination, and Carbonylation of Hydrocarbons: Alkane and Alkene Conversion to Sulfonic Acids, Ketones, and Aldehydes
Mercury-photosensitized sulfination of alkanes, RH, with SO2 forms sulfinic acids (RSOOH) and sulfinate esters (RSOOR) in high conversion and yield; oxidation of the mixture produces RSO2OH in high yield.Mercury-photosensitized hydrosulfination of alkenes with H2 and SO2 gives RSO2OH after oxidative workup.Mercury-photosensitized carbonylation of alkanes with CO gives RCHO and R2CO.
Ferguson, Richard R.,Crabtree, Robert H.
p. 5503 - 5510
(2007/10/02)
Process for producing aryl alpha-haloalkyl sulfones
A process for preparing alkenes by reaction of various sulfone substrates with carbon tetrahalide in the presence of a strong base. The reactions are accelerated by the presence of a polar compound. Sulfone carbanions attack the carbon tetrahalide to produce an α-halogenated intermediate and a dihalocarbene. α-Halosulfones having α' hydrogens are converted to alkenes in situ via the Ramberg-Backland reaction. Sulfones having α but no α' hydrogens are simply α-halogenated. The dihalocarbene generated in the reaction may attack the product, solvent, or another substrate to form other products. Alkenes produced by reaction of carbon tetrahalides with di-sec-alkyl sulfones are readily attacked by dihalocarbene to form the alkene-dihalocarbene adduct (a substituted 1,1-dihalocyclopropane).
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(2008/06/13)
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