Amide mercaptals

Amide mercaptals Dithiocarbamic acid esters Dithiourethans Iminodisulfides Iminodithiocarbonic acid esters... 

Amide mercaptals from amide acetals 595. (CH3)2NCH(0CH3)2 + 2 HSQHig-n... 

Amide mercaptals Dithiocarbamic acid esters 1,3-Dithiolanium salts,... 

Amide mercaptals Di(alkylthio)-N,N-dimethyl-methylamines 20 Dithiocarbamic acids and esters Dithiocarbamidium salts Dithiocarboxylic acid ester S-imides... 

A stirred soln. of startg. mercaptal in 9 1 methanol/water treated with (CF3C02)2lPh, and stirred at room temp, for 2 min 6-acetoxyhexanal. Y 85%. The method is mild, rapid, and leaves a variety of functional groups unaffected esters, nitriles, secondary amides, alcohols, halides, alkenes, alkynes, amines, and thioesters. F.e., also acetals in pure alcoholic media, s. G. Stork, K. Zhao, Tetrahedron Letters 30, 287-90 (1989). 

Methylthio-l,2-dithiolium perchlorates may be obtained directly from keten mercaptals, for example (31), by the action of phosphorus pentasulphide and subsequent treatment of the insoluble residue with perchloric acid. Similar treatment of /3-keto-amides (32) yields 3-arylimino-l,2-dithiole perchlorates (27 R = Ar, X = CIO4). The method succeeds with amides (32 R = alkyl) and thus serves as a route to the previously inaccessible 5-alkyl-l,2-dithiol-3-imines. Demethylation of 3-methylthio-5-phenyl-l,2-dithiolium cation, to give 3-phenyl-l,2-dithiole-3-thione, occurs when the iodide is heated in xylene. 

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