3715-92-2Relevant academic research and scientific papers
The reaction of ethylenethiourea with nitrite and transnitrosation by N-nitrosoethylenethiourea
Yamamoto,Yamada,Tanimura
, p. 3678 - 3683 (1983)
Ethylenethiourea (ETU), a degradation and metabolic product of ethylenebisdithiocarbamate fungicides, was nitrosated by NaNO2 to form N-nitrosoethylenethiourea (NETU), ETU was nitrosated much more rapidly than morpholine and methylurea, which are easily nitrosatable compounds, and NETU formation increased with lowering of the pH. NETU was most unstable around pH 10 and was rather stable in strongly alkaline media above pH 12. The main decomposition reaction of NETU in acidic media was denitrosation. Transnitrosation by NETU to secondary amines gave high yields of nitrosamines at pH 3 and even at pH 5.
The Nitrosation of NN'-Dialkylthioureas
Meijide, Fransisco,Stedman, Geoffrey
, p. 1087 - 1090 (1988)
The reaction between nitrous acid and NN'-dimethylthiourea and imidazolidine-2-thione (ethylenethiourea) involves a rapid, reversible initial nitrosation at sulphur, followed by a slower transfer of the nitroso group to the secondary amino group to form an N-nitrosothiourea.The kinetics exclude the possibility of the N-nitroso compound being formed by direct N-nitrosation and require the S-nitroso compound to be a precursor.The conversion of the S-nitrosoalkylthiourea into the N-nitroso product involves rate-determining proton loss to form an intermediate which is partitioned between steps involving reprotonation and transfer of the nitroso group from sulphur to nitrogen.
