A facile one-pot conversion of aldehydes into nitriles

Synthetic Communications

Volumn 39, Issue 20, 2009, Pages 3601-3606

  Chill, Samuel T ^a   Mebane, Robert C ^a  

^a UNIVERSITY OF TENNESSEE AT CHATTANOOGA   (United States)

Author keywords

Aldehyde; Aldoxime; Dehydration; Nitrile; Tandem reaction

Indexed keywords

ALDEHYDE; DIMETHYL SULFOXIDE; HYDROXYLAMINE; NITRILE;

ARTICLE; CHEMICAL REACTION; SYNTHESIS; TEMPERATURE;

EID: 70349195184     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902788174     Document Type: Article

References (23)

1. Friedrich, K.; Waaensfesl, K. The Chemistry of the Cyano Group; Wiley-Interscience: New York, 1970.
2. Fatiadi, A. J. Preparation and Synthetic Applications of Cyano Compounds; Wiley: New York, 1983.
3. Mathew, C. T.; Su, H.; Wu, B. Preparation of organic nitriles from aldoximes. WO Patent 9805630 A, 1998.
4. Chihiro, M.; Nagamoto, H.; Takemura, I.; Kitano, K.; Komatsu, H.; Sekiguchi, K.; Tabuse, F.; Mori, T.; Tominaga, M.; Yabuuchi, Y. Novel thiazole derivatives as inhibitors of superoxide production by human neutrophils: Synthesis and structure-activity relationships. J. Med. Chem. 1995, 38, 353-358.
5. Serrano, J.; Sierra, T.; Gonzalez, Y.; Bolm, C.; Weickhardt, K.; Magnus, A.; Moli, G. Improving FLC properties: Simplicity, planarity, and rigidity in new chiral oxazoline derivatives. J. Am. Chem. Soc. 1995, 117, 8312-8321.
6. Medwid, J.; Paul, R.; Baker, J.; Brockman, J.; Du, M.; Hallet, W.; Hanifin, J.; Hardy, R.; Tarrant, M. Preparation of triazolo[1,5]pyrimidines as potential antiasthama agents. J. Med. Chem. 1990, 33, 1230-1241.
7. Mai, K.; Patil, G. Trichloromethyl carbonochloridate: A dehydrating reagent for the preparation of nitriles from aldoximes. Synthesis 1986, 12, 1037-1038.
8. Kim, S.; Kyu, Y. Y. Di-2-pyridyl sulfite. A new useful reagent for the preparation of N-sylfinylamines, nitriles, isocyanides, and carbodiimides under mild conditions. Tetrahedron Lett. 1986, 27, 1925-1928.
9. Telvekar, V. N.; Akamanchi, K. G. A simple system for preparation of protected glycosidic carbohydrate nitriles from corresponding oximes. Synth. Commun. 2004, 34, 2331.
10. Surgie, A. S. Converting aldehydes to nitriles under mild conditions: Reaction of dialkyl hydrogen phosphonates with oximes. J. Org. Chem. 1969, 34, 2805-2806.
11. Suzuki, H.; Fuchita, T.; Iwasa, A.; Mishina, T. Diphosphorous tetrachloride as a reagent for converting epoxides into olefins and aldoximes into nitriles under mild conditions. Synthesis 1978, 4, 905-908.
12. Foley, H. G.; Dalton, D. R. Neutral conversion of aldoximes into nitriles at low temperature. J. Chem. Soc., Chem. Commun. 1973, 628.
13. Clive, D. L. A new method for conversion of aldoximes into nitriles: Use of chlorothionoformates. J. Chem. Soc., Chem. Commun. 1970, 1014.
14. Narsaiah, A. V.; Sreenu, D.; Nagaiah, K. Triphenylphosphine-iodine: An efficient reagent system for the synthesis of nitriles from aldoximes. Synth. Commun. 2006, 36, 137-143.
15. Hart-Davis, J.; Battioni, P.; Boucher, J.-L.; Mansuy, D. New catalytic properties of iron porphyrins: Model systems for cytochrome P450-catalyzed dehydration of aldoxime. J. Am. Chem. Soc. 1998, 120, 12524-12530.
16. Lehnert, W. Nitriles from oximes with TiCl4=pyridine under mild conditions. Tetrahedron Lett. 1971, 6, 559-560.
17. Sahu, S.; Patel, P.; Mishra, B. K. Selective oxidation of arylaldoximes by cetyltrimethylammonium dichromate to arylaldehydes and arylnitriles. Synth. Commun. 2005, 35, 3123-3126.
18. Attanasi, O.; Palma, P.; Serra-Zanetti, F. Effect of metal ions in organic synthesis, XVII:. Mild, easy, and high-yield conversion of aldoximes into nitriles under copper(II) acetate-catalysis. Synthesis 1983, 741-742.
19. Yang, S. H.; Chang, S. Highly efficient and catalytic conversion of aldoximes to nitriles. Org. Lett. 2001, 3, 4209-4211.
20. Choi, E.; Lee, C.; Na, Y.; Chang, S. [RuCl2(p-cymene)]2 on carbon: An efficient, selective, reusable, and environmentally versatile heterogeneous catalyst. Org. Lett. 2002, 4, 2369-2371.
21. Zuidema, D. R.; Dennison, A. L.; Park, E. Y.; Mebane, R. C. Conversion of aldoximes into nitriles with Raney nickel in refluxing 2-propanol. Synth. Commun. 2008, 38, 3810-3815.
22. Bruice, P. Y. Organic Chemistry, 5th Ed.; Pearson Prentice Hall: Upper Saddle River, NJ, 2007; p. 811.
23. Gaikwad, D. D.; Renukdas, S. V.; Kendre, B. V.; Shisodia, S. U.; Borade, R. M.; Shinde, P. S.; Chaudhary, S. S.; Pawar, R. P. Facile synthesis of nitriles from aromatic aldehydes using DMSO-I2. Synth. Commun. 2007, 37, 257-259.