Journal of the Chemical Society. Perkin transactions II p. 1087 - 1090 (1988)
Update date:2022-08-11
Topics:
Meijide, Fransisco
Stedman, Geoffrey
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.
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