Nef Reaction

J. U. Nef, Ann. 280, 263 (1894).

Formation of aldehydes and ketones from primary and secondary nitroalkanes, respectively, by treatment of their salts with sulfuric acid:

Modified conditions: W. Adam et al., Synlett 1998, 1335; P. Ceccherelli et al., Synth. Commun. 28, 3057 (1998). Application to spiroketals: T. Capecchi et al., Tetrahedron Letters 39, 5429 (1998). Reviews: P. Salomaa in The Chemistry of the Carbonyl Group, S. Patai, Ed. (Interscience, N.Y., 1966) pp 177-210; H. W. Pinnick, Org. React. 38, 655-792 (1990); D. S. Grierson, H.-P. Husson, Comp. Org. Syn. 6, 937-944 (1991).