Reviews thiols

Carbon monosulfide, CS, which can be produced by passiag CS2 through a high voltage discharge, can react with C H SCl at low temperatures ia toluene to give CgH SC(S)Cl. In a similar manner CS reacts with S2CI2 by double iasertion to yield C1C(S)SSC(S)C1 (9). Carbon monosulfide can also react with amines or thiols ia toluene or DMF (10). A review of the synthetic utiUty of CS has been pubUshed (11). 

The chemistry of organic sulfur compounds is very rich and organosulfur compounds are incorporated into many molecules. Thiols, or mercaptans as they were originally called, are essential as feedstocks in the manufacture of many types of mbber (qv) and plastics (qv). They are utilized as intermediates in agricultural chemicals, pharmaceuticals (qv), ia flavors and fragrances, and as animal feed supplements. Many reviews have been undertaken on the chemistry of the thiols, regarding both their preparation and their reactions (1 7). 

The heat capacities and entropies of organic compounds, including many thiols, have been compiled (19,20). The thermochemistry of thiols and other organosulfur compounds has been extensively reviewed (21). 

Gas-phase oxidation of thiols has been discussed in some depth (33). This review mainly emphasi2es atmospheric processes, but a section on nitrogen oxides and thiols appears to be broadly appHcable. The atmospheric oxidation chemistry of thiols is quite different from that of alcohols. 

A review of the role of thiols as electron donors in photoinduced electron-transfer reactions has been compiled (49). 

Thiol—Disulfide Interchange Reactions. The interchange between thiols and disulfides has been reviewed (50). This reaction is base-catalyzed. It involves the nucleophihc attack of a thiolate ion on a disulfide. This is shown in equations 35, 36, and 37. 

Metal Ion-Promoted Reactions of Thiols. Metal ion-promoted reactions of thiols have been reviewed (53). The bulk of the coverage concerns metal ion promoted aspects of sulfur chemistry. The main topics of interest are the formation of sulfenamides, sulfides, and disulfides using metal-mediated reactions. 

The toxicology and procedures for handling thiols used in gas odorants have been reviewed (56), as have thiols as a whole (57). A partial listing of toxicological results is shown in Table 4. 

Orthoesters, RC(OR )2 (1), thioesters, RCSOR ( A) Sulfur compounds Thiols), and carbamates, H2NCOOR, are not covered in this review. 

Sulfinyl chlorides may be prepared from the corresponding thiols or disulfides by oxidative reactions rather than by reductions of sulfonyl compounds. A recent example, which improves the earlier procedure of Douglass, is given by equation (3) . The chemistry of sulfinic acids and their derivatives has been reviewed . 

The progress on S-C bond activation, which covers the reduction of a C-S bond to a C-H bond, cross coupling reaction of sulfides with main group organometaUic nucleophiles, ring opening reactions of thietanes and thiiranes, and desulfurization of thiols, sulfides, and thiophenes has already been reviewed elsewhere [6-10], and... 

The potentially tautomeric side-chain thiol systems exist mainly in the thiol form in liquid solution and in the gas phase, as found by IR and NMR spectroscopy and by a study of ionization potentials.126 Upon alkylation using the ion-pair extraction method, only the S-alkylated compounds were obtained. The synthesis, reactions, and properties of some selenides of thiophene, furan, and selenophene have been reviewed.127... 

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