Sulfone, methylthiomethyl p-tolyl

Methylthiomethyl p-tolyl sulfone 257 was shown to react with various esters in the presence of excess NaH, affording compounds 263 which, upon reduction with NaBH4 and further treatment with alkali, can be converted to the corresponding aldehydes344. Oxidation of 263 with hydrogen peroxide gives S-methyl a-ketocarbothioates 264335. 

SCH2COOEt) ° and with methyl methylsulfinylmethyl sulfide (MeSCH2SOMe) or methylthiomethyl p-tolyl sulfone (MeSCH2S02C6H4Me) (to give ArCH2-SMe), in each case with a Lewis acid catalyst. 

Potassium nitrosodisulfonate, 258 Trimethylsilyl chlorochromate, 327 By hydrolysis of acetals or thioacetals Amberlyst ion-exchange resin, 152 Methylthiomethyl p-tolyl sulfone, 192 By isomerization of allylic alcohols N-Lithioethylenediamine, 157 By oxidation of aromatic side chains Trimethylsilyl chlorochromate, 327 From oxidative cleavage of alkenes [Bis(salicylidene-7-iminopropyl)-methylamine]cobalt(II)... 

From oxidative cleavage of 1,2-diols and 1,2-amino alcohols Dibutyltin oxide, 95 By reaction of alkyl halides with sulfur-stabilized carbanions Methylthiomethyl p-tolyl sulfone, 192 From reduction of carboxylic acids Vilsmeier reagent, 341 From terminal alkenes by addition reactions... 

By hydrolysis of ketals or thioketals Amberlyst ion-exchange resin, 152 Methylthiomethyl p-tolyl sulfone, 192 From oximes... 

Methylthiomethyl p-tolyl sulfone, 192 Potassium ruthenate, 259 Trimethylsilyl chlorochromate, 327 a-Substituted ketones (see also Halo carbonyl compounds, Hydroxy aldehydes and ketones) a-Acetoxy ketones Benzeneselenenyl chloride-Silver acetate, 27... 

Aldehydes Alkyidimesitylborane. Chloro-methyltrimethylsilane. Diethyl[(2-tetrahy-dropyranyloxy)methylphosphonate. N,N-Dimethylchloromethyleniminum chloride. Dimelhyl(methylthio)sulfonium tetrafluom-borate. Methoxy(phenylthio)methyllithium. Methylthiomethyl p-tolyl sulfone. 1-Phen-ylthio-1 -trimethylsilylethylene. Tetrakis-(Iriphcnylphosphine)palladium. Thexyl-chloroborane-Dimethyl sulfide. 

Methylthiomethyl p-tolyl sulfone, CH3SCH2S02C6H4CHrp (1). The sulfone is prepared by reaction of CH3SCH2OAc with p-CH3C6H4S02Na. 

Related Reagents. Benzothiazole Carbon Monoxide A, A -Diethylaminoacetonitrile iVJV-Dimethyldithiocarbamo-ylacetonitrile 2-Lithio-l,3-dithiane Methylthiomethyl p-Tolyl Sulfone 2- Trimethylsilyl)thiazole. 

Synthesis of Esters and Aldehydes. Monoalkylation of methylthiomethyl p-tolyl sulfone (MT-sulfone) with an alkyl halide is achieved by the action of a phase-transfer catalyst (PTC) in toluene-50% aq NaOH. sodium hydride and butyl-lithium also generate a carbanion of MT-sulfone. Arylmethyl derivatives of MT-sulfone are prepared by sodium borohydride reduction of the Knoevenagel condensation products with aromatic aldehydes. The monoalkylated products are converted into the corresponding methyl esters (eq 1). This functionalization can be utilized for synthesizing a-alkoxy carboxylic esters (eq 2) and Q -amino acids (eq 3). ... 

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