Dehydration of Aldoximes to Nitriles Using a Polymeric Reagent

Abstract

Aldoximes undergo rapid dehydration with polyvinylpyrrolidone–thionyl chloride complex under mild reaction conditions to afford nitriles in high yields

References

1. K. Friedrich and K. Waaensfels, The Chemistry of Cyano Group, ed. Z. Rappoport, Wiley-Interscience, New York, 1970; D. T. Mowry, Chem. Rev., 1948, 42, 250.
2. G. A. Olah, S. C. Narang and A. Garcia-Luna, Synthesis, 1980, 659.
3. G. A. Olah, Y. D. Vankar and A. Garcia-Luna, Synthesis, 1979, 227.
4. H. Suzuki, T. Fuchita, A. Iwasa and T. Mishina, Synthesis, 1978, 905.
5. H. G. Foley and D. R. Dalton, J. Chem. Soc., Chem. Commun., 1973, 628.
6. D. L. Clive, J. Chem. Soc., Chem. Commun., 1970, 1014.
7. G. A. Olah and Y. D. Vanker, Synthesis, 1978, 702.
8. G. Rosini, G. Baccolini and S. Cacchi, J. Org. Chem., 1973, 38, 1060.
9. W. Lehnert, Tetrahedron Lett., 1971, 6, 559.
10. A. S. Surgie, J. Org. Chem., 1969, 34, 2805.
11. M. Rogic, J. F. Van Paooen, K. P. Klein and T. P. Demmin, J. Org. Chem., 1974, 39, 3424.
12. C. R. Harrison, P. Hodge and W. J. Rogers, Synthesis, 1977, 41.
13. T. Keumi, T. Yamamoto, T. Saga and H. Kitajima, Bull. Chem. Soc. Jpn., 1981, 54, 1579.
14. P. Molina, M. Alajarin and M. J. Vilaplana, Synthesis, 1982, 1016.
15. A. Arrieta and C. Palomo, Synthesis, 1983, 472.
16. M. Shinozaki, M. Imaizumi and M. Tajima, Chem. Lett., 1983, 929.
17. M. Narayana Rao, P. Kumar and K. Garyaki, Org. Prep. Proced Int., 1989, 21, 230.
18. H. M. Meshram, Synthesis, 1992, 943.
19. A. R. Katritzky, G. F. Zhang and W. G. Fan, Org. Prep. Proced Int., 1993, 25, 315.
20. A. R. Bandger, S. R. Jagtap and S. B. Ghodeshwar, Synth. Commun., 1995, 25, 2993.
21. H. M. S. Kumar, P. K. Mohanty and M. S. Kumar, Synth. Commun., 1997, 27, 1327.
22. Y. H. Kim and J. M. Shin, Tetrahedron Lett., 1985, 26, 3821.
23. S. Kim and K. Y. Yi, Tetrahedron Lett., 1986, 27, 1925.
24. A. R. Kiasat, Ph.D. Thesis, Shiraz University, Shiraz, Iran, 1998.
25. F. Hiashi and T. Nishi, J. Polym. Sci., Part A, Polym. Chem., 1986, 24, 701.
26. M. S. Newman and P. K. Sujeeth, J. Org. Chem., 1978, 43, 4367.
27. A. Saednya, Synthesis, 1983, 748.
28. K. Mai and G. Patil, Synthesis, 1986, 1037.
29. Fluka Handbook of Fine Chemicals, 1993–1994.
30. A. I. Vogel, A Text Book of Practical Organic Chemistry, 4th edn., Elbs and Longman, 1978.