User:UmichSSGleader/History
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.
History
[edit]Julie Colbath Christina Lee Courtney Tipton Stacey Van Buskirk
History of the Ritter Reaction
• This reaction is named after John J. Ritter.
• P. Paul Minieri submitted a thesis to the Graduate School of New York University in May 1948 in order to fulfill the requirements for the degree of Doctor of Philosophy.
• Ritter and Minieri collaborated and performed the experiment.
• The analysis was performed in the Microchemistry Laboratory at NYU.
• “The interaction of nitriles and alkenes in the presence of concentrated sulfuric acid has been shown to result in N-alkyl amides. A series of such amides has been prepared and characterized, and the structures of typical members have been verified by hydrolysis to the corresponding amines.” This is the summary of the experiment.
• The purpose was to convert nitriles and alkenes to amides using concentrated sulfuric acid. Ritter and Minieri characterized the product to confirm that it was a N-alkyl amide.
• Their work was originally published in the Journal of the American Chemical Society in 1948.
• Indinavir (Crixivan), a HIV protease inhibitor, is created using the Ritter Reaction. Therefore, it has significance in pharmaceutical synthesis.
Ritter, J. J.; Minieri, P. P. J. Am. Chem. Soc. 1948, 70, 4045-4048.
Ritter, J. J., Kalish, J.; J. Am. Chem. Soc. 1948, 70, 4048.
Ritter, J. J., Kalish, J.; Organic Syntheses, Coll. Vol. 5, p.471 (1973); Vol. 44, p.44 (1964)
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)