Bouveault Aldehyde Synthesis

L. Bouveault, Bull. Soc. Chim. France 31, 1306, 1322 (1904).

Action of Grignard or organic lithium reagents on N,N-disubstituted formamides yields the homologous aldehydes:

L. I. Smith, J. Nichols, J. Org. Chem. 6, 489 (1941); J. Sicé J. Am. Chem. Soc. 75, 3697 (1953); E. R. H. Jones et al., J. Chem. Soc. 1958, 1054. Use of lithio derivatives instead of Grignard reagents: E. A. Evans, Chem. & Ind. (London) 1957, 1596. Synthetic applications using modified conditions: C. Pétrier et al., Tetrahedron Letters 23, 3361 (1982); J. Einhorn, J. L. Luche, ibid. 27, 1791 (1986); H. Meier, H. Aust, J. Prakt. Chem. 341, 466 (1999). Cf. Bodroux-Chichibabin Aldehyde Synthesis.