Sulfenic acid esters

M. Charton, in The Chemistry of Sulfenic Acids, Esters and Derivatives (Ed. S. Patai), Wiley, Chichester, 1990, pp. 657-700. 

Sulfenic acids, esters and halides are reduced to thiols by many reagents, e.g. hydrazine, lithium aluminium hydride and metallic sodium. These addition reactions are extensively employed for trapping sulfenic acids, e.g. with ethyl acrylate (57) to give the adduct (58) (Scheme 32). 

Stilbenes synthesis by Heck coupling, 43 Stille coupling aryl triflate + organylstannane, 42 Stobbe condensation, 58-59 Stork reagent, 328-329 Strain, steric. See Steric strain Strecker s synthesis of a-amino acids, 50, 301 L-Streptose synthesis, 267 Styrene. See Benzene, ethenyl-Succinic acid. See Butanedioic acid Succinimide. See 2,5-Pyrrolidinedione Sugars. See Monosaccharides Oligosaccharides inexpensive derivs. pr. (table), 263-264 Sulfafurazole, 307 Sulfamethoxazole, 308 Sulfenic acids, esters ... 

Sulfenic acid esters from alcohols and reverse reaction Protection of nucleoside hydroxyl... 

Glycosides from thioglycosides and sulfenic acid esters Stereospecific conversion under mild conditions... 

Disaccharides. A mixture of startg. thioglycoside, sulfenic acid ester, and 4A molecular sieves in acetonitrile treated with trimethylsilyl triflate at — 35° under N2, stirred at the same temp, for 40 min, and worked up with NEt3 product. Y 90% (a/ 3 5 95). The stereoselectivity was solvent-dependent, being a-selective in ether and P-selective in acetonitrile. F.e. and substituent effects s. Y. Ito, T. Ogawa, Tetrahedron Letters 28, 4701 (1987). 

Alkoxysulfonium salts Sulfenic acid esters Sulfoxides Sulfoxonium salts... 

X0 compds. 24, 126 sulfenic acid esters 27, 272 sulfonium salts 27, 224 thioethers 28,174 -, 1-monohalogenation 26, 526... 

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