Hofmann Isonitrile Synthesis (Carbylamine Reaction)

A. W. Hofmann, Ann. 146, 107 (1868); Ber. 3, 767 (1870).

Formation of isonitriles by the reaction of primary amines with chloroform in the presence of alkali; the odor of the isocyanide is a test for a primary amine:

P. A. S. Smith, N. W. Kalenda, J. Org. Chem. 23, 1599 (1958); M. B. Frankel et al., Tetrahedron Letters 1959, 5; H. L. Jackson, B. C. McKusick, Org. Syn. coll. vol. IV, 438 (1963); W. P. Weber, G. W. Gokel, Tetrahedron Letters 1972, 1637.