Stephen Aldehyde Synthesis

H. Stephen, J. Chem. Soc. 127, 1874 (1925); T. Stephen, H. Stephen, ibid. 1956, 4695.

Reaction sequence employed to convert nitriles to aldehydes. Treatment of the nitrile with a mixture of stannous chloride and hydrochloric acid yields the imine salt complex which is subsequently hydrolyzed to the aldehyde. Practically applied only to aromatic aldehydes:

L. N. Ferguson, Chem. Rev. 38, 243 (1946); E. Mosettig, Org. React. 8, 246 (1954); O. Bayer, Houben-Weyl 7/1, 299 (1954); E. N. Zilberman, P. S. Pyryalova, J. Gen. Chem. U.S.S.R. (Engl. trans.) 33, 3348 (1963); C. G. Stuckwisch, J. Org. Chem. 37, 318 (1972). Cf. Grundmann Aldehyde Synthesis; Sonn-Müller Method.