One-carbon fragment which can behave as a nucleophile or an electrophile. Alkylating agents give N,N-dialkyl cyanamides which readily undergo hydrolysis to dialkylamines: Synthesis, 882 (1978).
Useful building block for heterocyclic synthesis. Reaction with o-phenylenediamines gives 2-aminobenzimidazoles: Angew. Chem. Int. Ed., 12, 841 (1973). With 4-(1-Cyclohexen-1-yl)-morpholine, and elemental sulfur, a 2-aminothiazole is formed in good yield: J. Prakt. Chem., 312, 776 (1970).
In the presence of NBS, undergoes addition to alkenes. The products are converted to N-cyanoaziridines by base: Tetrahedron Lett., 1125 (1970), or in the presence of acid, cyclization gives an imidazoline, which can be converted to the vic-diamine: J. Am. Chem. Soc., 105, 4106 (1983); Tetrahedron Lett., 25, 399 (1984).
