Methyl phenylthio ether, oxidation

Steele, W.V., Chirico, R.D., Cowell, A.B., Knipmeyer, S.E., and Nguyen, A. Thermodynamic properties and ideal-gas enthalpies of formation for 2-aminoisobutyric acid (2-methylalanine), acetic acid, ( -5-ethylidene-2-norbornene, mesityl oxide (4-methyl-3-penten-2-one), 4-methylpent-l-ene, 2,2 -bis(phenylthio)propane, and glycidyl phenyl ether (1,2-epoxy-3-phenox3q>ropane), / Chem. Eng. Data, 42(6) 1053-1066, 1997. 

Unsaturated 1,5-dicarbonyl compounds. The phenylthioalkylation of silyl enol ethers of carbonyl compounds (9, 521-522) can be extended to the synthesis of unsaturated 1,5-dicarbonyl compounds. In a typical reaction the enol silyl ether of a ketone is alkylated with the unsaturated chloride 1 under ZnBr2 catalysis to give a homoallyl sulfide. Ozonolysis of the methylene group is accompanied by oxidation of the phenylthio group sulfoxide elimination results in an unsaturated 1,5-aldehydo ketone (equation I). Alkylation with 2 results in a methyl ketone (equation II). 

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