Methane sulfenyl chloride

Methionine 149 is a very important amino acid, and several stereospecifically labeled samples have been prepared. Golding and others (140,141) prepared samples of ( )- and (Z)-[l, 2- H2]ethylene ISO, H = He = H, and 150, Ha = Hb = H, respectively, from [ HjJacetylene and converted these to the corresponding chlorides 151 by anti addition of methane sulfenyl chloride. Substitution by sodium acetylaminomalonate gave the products 152, the reaction occurring with retention of configuration via a thiiranium ion intermediate (Scheme 47). 

To the more inert double bond of unsaturated piperazinediones methane sulfenyl chloride or sulfur chloride was added, the p-thio compounds being formed in every case 444). 

However, even at room temperature a fast isomerization takes place to sulfenyl chlorides containing the appropriately fluorinated trihalo-methane ... 

Sulfenyl Chloride Dichloro-fluoro-methane ElOa, 249 (CS —... 

Sulfenyl Chloride Diehloro-fluoro-methane E10b2, 73 (Educt)... 

The resin-bound fragment preparation starts with the chlorine displacement from the chloromethylene function on chloromethylated polystyrene by the cesium salt of Z-L-Cys(Trt)-OH. The resulting benzyl ester is treated with methoxy-carbonyl sulfenyl chloride (Scm-Cl) to form the active intermediate sulfenyl thiocarbonate which is allowed to react with 4-acyloxy-6-mercaptodibenzofuran, preferably in dichloro-methane-hexafluoro-2-propanol, with or without catalytic triethy-lamine to afford the unsymmetrical disulfide (eq 2) ... 

Dicarbonyl compounds. The adducts (2) of the anion (1) of meth-oxy(phenylthio)methane and aldehydes (12, 316) are converted into a-sulfenyl aldehydes (3) on treatment with methanesulfonyl chloride and triethylamine (1 1). Reaction of 3 with a Wittig or Wittig-Horner reagent followed by isomerization... 

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