|
Sulfenamides (also spelled sulphenamides) are a class of organosulfur compounds characterized by the general formula RSNR'2, where R and R' are H, alkyl, or aryl.〔Capozzi, G., Modena, G., Pasquato, L. in "Chemistry of Sulphenyl Halides and Sulfenamides" ''The Chemistry of Sulphenic Acids and their derivatives''. Ed. Saul Patai. John Wiley & Sons Ltd. Chapter 10. 403-516, 1990. 〕 Sulfenamides have been used extensively in the vulcanization of rubber using sulfur. They are related to the oxidized compounds sulfinamides (RS(O)NR'2) and sulfonamides (RSN(O)2R'2). ==Preparation== Sulfenamides are usually prepared by the reaction of sulfenyl chlorides and amines:〔 :RSCl + R'2NH → RSNR'2 + HCl The S-N bond formation generally obeys standard bimolecular nucleophilic substitution rules, with the basic nitrogen centre being the nucleophile. Primary sulfenamide formation as shown above occurs with the reaction of the sulfenyl halide with ammonia. Additionally primary as well as secondary and tertiary amines form sulfenamides through reaction with, thiols, disulfides, and sulfenyl thiocyanates.〔Drabowicz, J., Kielbasinski, P., Mikoiajczyk, M. (1990). "Synthesis of Sulphenyl Halides and Sulphenamides". ''The Chemistry of Sulphenic Acids and their derivatives''. Ed. Saul Patai. John Wiley & Sons Ltd.. Chapter 6. 221-292. 〕 In one illustrative synthesis, triphenylmethanesulphenyl chloride and butylamine react in benzene at 25 C: :Ph3CSCl + 2BuNH2 → Ph3CSN(H)Bu + BuNH3Cl Many other routes to sulfenamides are known, starting from thiols and disulfides.〔I V Koval' "Synthesis and Application of Sulfenamides" Russian Chemical Reviews, 1996, Volume 65, 〕 :RSSR + 2R'2NH + Ag+ → RSNR'2 + AgSR + R'2NH2+ 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Sulfenamide」の詳細全文を読む スポンサード リンク
|