P(RNCH2CH2)3N: A versatile and efficient catalyst for the conversion of aldoximes to nitriles

Heteroatom Chemistry

Volumn 10, Issue 7, 1999, Pages 541-543

  Fei, Xiang Shu ^a   Verkade, John G ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000058383     PISSN: 10427163     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-1071(1999)10:7<541::AID-HC4>3.0.CO;2-B     Document Type: Article

References (22)

1. Friedrich, K.; Wallenfels, K. The Chemistry of the Cyano Group; Rappoport, Z., Ed.; Interscience: New York, 1970, pp 92-93.
2. Meshram, H. M. Synthesis 1992, 943.
3. Narayan Rao M.; Kumar, P.; Garyali K. Org Prep Proceed Int 1989, 21, 230.
4. Bandgar, B. P.; Jagtap S. R.; Ghodeshwar S. R.; Wadgaonkar P. P. Synth Commun 1995, 25, 2993.
5. Olah, G. A.; Vankar, Y. D. Synthesis 1978, 702.
6. Olah, G. A.; Narang, S. C.; Garcia-Luna, A. Synthesis 1980, 659.
7. Kim, J. N.; Chung, K. H.; Ryu, E. K. Synth Commun 1990, 20, 2785.
8. Sabitha, G.; Syamala, M. Synth Commun 1998, 28, 4577, and references therein.
9. Tang J. S.; Verkade, J. G. Angew Chem Int Ed Engl 1993, 32, 896;
10. (b) Tang, J. S.; Verkade, J. G. J Org Chem 1994, 59, 7793;
11. (c) D'Sa, B. A.; Verkade, J. G. J Org Chem 1996, 61, 2963;
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13. (e) Arumugam, S.; McLeod, D.; Verkade; J. G. J Org Chem 1997, 62, 4827;
14. (f) D'Sa, B. A.; Kisanga, P.; Verkade, J. G. J Org Chem 1998, 63, 3961;
15. (g) Wang, Z.; Verkade; J. G. Heteroat Chem 1998, 9, 687.
16. Benzaldoxime, 4-F-benzaldoxime, and cyclohexane-carbonitrile were obtained from Aldrich. Other oximes were prepared by standard methods (see Vogel, A.L. A Text Book of Practical Organic Chemistry, 3rd ed.; Longmans, Green, and Co.: New York, 1956).
17. CRC Handbook of Data on Organic Compounds; Lide, D.R.; Milne, G.W.A., Eds. CRC Press: Boca Raton, Florida, 1994.
18. (a) Pouchert, C. J. The Aldrich Library of FTIR Spectra, Vol 3, 1st ed.; Aldrich Chemical Company Milwaukee, 1985; 795, 1399;
19. (b) Orsini, F. Synthesis 1985, 500;
20. (c) Sosnovsky, G.; Krogh, J. A. Synthesis 1978, 703.
21. 1H FT NMR Spectra; Vol. 1; Aldrich Chemical Company: Milwaukee, 1985; 1351-1416;
22. (b) ibid. Vol. 2, 1479-1575.