Abstract
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 ▪ transformation is also found to take place in gastric juice.
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