Ritter reaction

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The Ritter reaction is a chemical reaction that transforms a nitrile into a N-tert-butyl amide using strong acid and isobutylene.^[1][2][3]

Recently, tert-butyl acetate has been shown to be an easy to handle substitute for isobutylene.^[4] Benzylic^[5] and tertiary^[6] alcohols also successfully react with nitriles to form amides via the Ritter reaction.

[edit] Reaction mechanism

The Ritter reaction proceeds by the nucleophilic addition of a nitrile to the carbenium ion 2. The resulting nitrilium ion 3 is hydrolyzed by water to the desired amide 5.

[edit] References

1. ↑  Ritter, J. J.; Minieri, P. P.; J. Am. Chem. Soc. 1948, 70, 4045.
2. ↑  Ritter, J. J.; Kalish, J.; J. Am. Chem. Soc. 1948, 70, 4048.
3. ↑  Krimen, L. I.; Cota, D. J.; Org. React. 1969, 17, 213-325. (Review)
4. ↑  Reddy, K. L. Tetrahedron Lett. 2003, 44, 1453-1455.
5. ↑  Parris, C. L. Organic Syntheses, Coll. Vol. 5, p.73 (1973); Vol. 42, p.16 (1962). (Article)
6. ↑  Ritter, J. J.; Kalish, J. Organic Syntheses, Coll. Vol. 5, p.471 (1973); Vol. 44, p.44 (1964). (Article)