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The Ritter reaction is a chemical reaction that transforms a nitrile into a N-alkyl amide using various alkylating reagents, for example, strong acid and isobutylene.[1][2][3]
Primary[4], secondary[5], tertiary[6], and benzylic[7] alcohols, as well as tert-butyl acetate[8], also successfully react with nitriles in the presence of strong acids to form amides via the Ritter reaction.
Reaction mechanism
[edit]The Ritter reaction proceeds by the electrophilic addition of either the carbenium ion 2 or covalent species[9][10] to the nitrile. The resulting nitrilium ion 3 is hydrolyzed by water to the desired amide 5.
References
[edit]- ^ Ritter, J. J., Minieri, P. P.; J. Am. Chem. Soc. 1948, 70, 4045.
- ^ Ritter, J. J., Kalish, J.; J. Am. Chem. Soc. 1948, 70, 4048.
- ^ Krimen, L. I., Cota, D. J.; Org. React. 1969, 17, 213-325. (Review)
- ^ Lebedev, M. Y., Erman, M. B.; Tetrahedron Lett. 2002, 43, 1397-1399. (Article)
- ^ Bishop, R.; In Comp. Org. Synth.; Trost, B.M., Fleming, I.; Eds.; Pergamon Press: New York, 1992; Vol. 6, 261-300. (Review)
- ^ Ritter, J. J., Kalish, J.; Organic Syntheses, Coll. Vol. 5, p.471 (1973); Vol. 44, p.44 (1964). (Article)
- ^ Parris, C. L.; Organic Syntheses, Coll. Vol. 5, p.73 (1973); Vol. 42, p.16 (1962). (Article)
- ^ Fernholz, H., Schmidt, H.J.; Angew. Chem., Int. Ed. Eng., 1969, 8, 521. (Article)
- ^ Booth, B.L., Jibodu, K.O., Proenca, F.J.R.P.; J. Chem. Soc., Perkin Trans. 1, 1983, 1067 - 1073, (Article)
- ^ Martínez, A.G., Alvarez, R.M., Vilar, E.T., Fraile, A.G., Hanack ,M., Subramanian, L. R.; Tetrahedron Lett. 1989, 30, 581-582. (Article)