Cannizzaro Reaction

S. Cannizzaro, Ann. 88, 129 (1853); K. List, H. Limpricht, Ann. 90, 180 (1854).

Base-catalyzed disproportionation reaction of aromatic or aliphatic aldehydes with no α-hydrogen to corresponding acid and alcohol. If the aldehydes are different, the reaction is called the “crossed Cannizarro reaction”:

T. A. Geissman, Org. React. 2, 94 (1944); F. P. B. Van der Maeden et al., Rec. Trav. Chim. Pays-Bas 91(2), 221 (1972); C. G. Swain et al., J. Am. Chem. Soc. 101, 3576 (1979); R. S. McDonald, C. E. Sibley, Can. J. Chem. 59, 1061 (1981). Review: T. Lane, A. Plagens, Named Organic Reactions (John Wiley & Sons, Chichester, 1998) p 40-42. Cf. Meerwein-Ponndorf-Verley Reduction; Oppenauer Oxidation; Tishchenko Reaction.