Direct oxidative conversion of aldehydes to nitriles using IBX in aqueous ammonia

Tetrahedron Letters

Volumn 48, Issue 21, 2007, Pages 3651-3653

  Arote, Nitin D ^a   Bhalerao, Dinesh S ^a   Akamanchi, Krishnacharya G ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aldehyde; Ammonia water; IBX; Nitrile; Oxidation

Indexed keywords

2 IODOBENZOIC ACID; ALDEHYDE DERIVATIVE; AMMONIA; NITRILE;

AQUEOUS SOLUTION; ARTICLE; BIOTRANSFORMATION; CHEMICAL STRUCTURE; MOLECULAR STABILITY; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 34247214463     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.137     Document Type: Article

References (23)

1. Varvoglis A. Hypervalent Iodine in Organic Synthesis (1997), Academic Press, London
2. Wirth T., and Hirt U.H. Synthesis (1999) 1271
3. Mowry D.T. Chem. Rev. 42 (1948) 250
4. Friedrich K., and Wallensfels K. In: Rappoport Z. (Ed). The Chemistry of the Cyano Group (1970), Wiley-Intersience, New York
5. North M. In: Katritzky A.R., Meth-Cohn O., and Rees C.W. (Eds). Comprehensive Organic Functional Group Transformation (1995), Pergamon, Oxford 617
6. Wang E.C., and Lin G.J. Tetrahedron Lett. 39 (1998) 4047
7. Miller C.P., and Kaufman D.H. Synlett (2000) 1169
8. Das B., Ramesh C., and Madhusudhan P. Synlett (2000) 1599
9. Nishiyama K., Oba M., and Watanabe A. Tetrahedron 43 (1987) 693
10. Elmorsy S.S., El-Ahl A.-A.S., Soliman H., and Amer F.A. Tetrahedron Lett. 36 (1995) 2639
11. Suziki H., and Nakaya C. Synthesis (1992) 641
12. Brackman W., and Smit P. J. Recl. Trev. Chim. 82 (1963) 757
13. Parameswaram K.N., and Friedman O.M. Chem. Ind. (London) (1965) 988
14. Misono A., Osa T., and Koda S. Bull. Chem. Soc. Jpn. 39 (1966) 854
15. Sato R., Itoh Y., Itep K., Nihina H., Goto T., and Saito M. Chem. Lett. (1984) 1913
16. Erman M.B., Snow J.W., and Williams M.J. Tetrahedron Lett. 41 (2000) 6749
17. Talukdar S., Hsu J.L., Chou T.C., and Fang J.M. Tetrahedron Lett. 42 (2001) 1103
18. Bandgar B.P., and Makone S.S. Synth. Commun. 36 (2006) 1347
19. Shukla V.G., Salgaonkar P.D., and Akamanchi K.G. J. Org. Chem. 68 (2003) 5422
20. Shukla V.G., Salgaonkar P.D., and Akamanchi K.G. Synlett 9 (2005) 1483
21. Bhalerao D.S., Mahajan U.S., Chaudhari K.H., and Akamanchi K.G. J. Org. Chem. 72 (2007) 662
22. Aldehyde (5 mmol) was added to a stirred solution of IBX (7.5 mmol) in aqueous ammonia (20 ml of a 28-30% solution, Sp. gravity = 0.89) and acetonitrile (3 ml) at room temperature. The resultant clear solution became turbid as the reaction proceeded. After completion of the reaction as indicated by TLC, the reaction mixture was diluted with water and extracted with ethyl acetate (2 × 25 ml). The combined organic layer was washed successively with water (2 × 25 ml), and brine (25 ml), dried over sodium sulfate and concentrated under vacuo to afford practically pure nitrile.
23. Frigerio M., Santagostino M., and Sputore S. J. Org. Chem. 64 (1999) 4537