Synthesis of Novel N-Nitrosothioureas and Examination of Their Mechanisms of Formation by High-Field Nitrogen-15 and Carbon-13 Nuclear Magnetic Resonance Spectra of Specifically Labeled Compounds

Article abstract of DOI:10.1021/jo00152a019

An examination by ¹⁵N NMR of Na¹⁵NO2 under various conditions of acidity led to the identification of several electrophilic nitrogen species.This permitted the selection of reaction conditions of low acidity which favor nitrosation at the nitrogen atom of thioureas rather than on the normally more reactive sulfur, leading to the isolation of novel N-nitrosothioureas.In contrast it was shown by employing ¹⁵N and ¹³C labeling that higher acidity conditions favor reaction via a detectable thionitrosyl intermediate.