von Braun Reaction

J. von Braun, Ber. 40, 3914 (1907); 42, 2219 (1909); 44, 1250 (1911).

Reaction of tertiary amines with cyanogen bromide to form disubstituted cyanamides and an alkyl halide:



Mechanistic correlation with Ritter, Bischler-Napieralski, Beckmann and Schmidt reactions, q.q.v.: G. Fodor, S. Nagubandi, Tetrahedron 36, 1279 (1980). Synthetic applications: S. Siddiqui et al., Z. Naturforsch. 37b, 1481 (1982); idem et al., Pakistan J. Sci. Ind. Res. 30, 163 (1987). Reviews: H. A. Hageman, Org. React. 7, 198-262 (1953); J. H. Cooley, E. J. Evain, Synthesis 1989, 1-7.