Tetrahedron p. 469 - 474 (1983)
Update date:2022-08-11
Topics:
Jorgensen, K. A.
El-Wassimy, M. T. M.
Lawesson, S. -O.
N-nitrosopiperidine and N-nitroso-N-methylaniline react in acidic solution with thiocarbonyl compounds to give the corresponding carbonyl analogues.Secondary- and tertiary thioamides, xanthione, thio- and dithiobutyrolactone, thiocoumarin, certain thiourea derivatives, dithio-O,O-thiocarbonic, S,S-trithiocarbonic- and N,N disubstituted thiocarbamic esters are all converted into the corresponding O-analogues.Thiobenzamide and N-phenylthiourea yield 1,2,4-thiadiazoles.All the reactions are run with iodide (I-) as NO+-carrier.The kinetics of the reaction have been studied under pseudo-first order conditions, and the reaction rate is proportional to the Pearson's nucleophilicity parameter of ions.The =C=S <*> =C=O transformation is also found to take place in gastric juice.
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