Conversion of Alcohols, Thiols, and Trimethysilyl Ethers to Alkyl Cyanides Using Triphenylphosphine/2,3-Dichlorol-5,6-dicyanobenzoquinone/n-Bu 4NCN

Journal of Organic Chemistry

Volumn 69, Issue 7, 2004, Pages 2562-2564

  Iranpoor, Nasser ^a   Firouzabadi, Habib ^a   Akhlaghinia, Batool ^a,b   Nowrouzi, Najmeh ^a  

^a SHIRAZ UNIVERSITY   (Iran)

^b DAMGHAN UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ETHERS;

ALKYL CYANIDES; THIOLS;

AROMATIC HYDROCARBONS;

2,3 DICHLORO 5,6 DICYANOBENZOQUINONE; ALCOHOL; ALKYL GROUP; BENZOQUINONE DERIVATIVE; CYANIDE; ETHER DERIVATIVE; NITRILE; THIOL DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TEMPERATURE;

EID: 1842503802     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035238v     Document Type: Article

References (21)

1. (a) Lease, T. G.; Shea, K. J. J. Am. Chem. Soc. 1993, 115, 2248.
2. (b) Gwaltney, S. L.; Sakata, S. T.; Shea, K. J. J. Org. Chem. 1996, 61, 7438.
3. (c) Fleming, F. F.; Huang, A.; Sharief, V. A.; Pu, Y. J. Org. Chem. 1997, 62, 3063.
4. The Chemistry of the Triple-Bond Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley-Interscience: New York, 1983.
5. The Chemistry of Cyano Group; Rappoport, Z., Ed.; Wiley-Interscience: New York, 1970.
6. Kornblum, N.; Smiley, R. A.; Blackwood, R. K.; Iffland, D. C. J. Am. Chem. Soc. 1955, 77, 6269.
7. (a) Castro, B. R. Org. React. 1983, 29, 1.
8. (b) Grundman, C. In Mothoden der Organischen Chemie (Houben-Weyl); Georg Thieme Verlag: Stuttgart, Germany, 1985; Vol. E5, p 1474
9. (c) Brett, D.; Downie, I. M.; Lee, J. B. J. Org. Chem. 1987, 32, 855.
10. (d) Castro, B.; Selve, C. Bull. Soc. Chim. Fr. 1971, 2296.
11. (e) Biogegrain, R.; Castro, B.; Selve, C. Tetrahedron Lett. 1975, 30, 2529.
12. (f) Mizuno, A.; Hamada, Y.; Shioiri, T. Synthesis 1980, 1007.
13. (g) Davis, R.; Untch, K. G. J. Org. Chem. 1981, 46, 2985.
14. (a) Mitsunobu, O. Synthesis 1981, 1.
15. (b) Hughes, D. L. Org. React. 1992, 42, 335.
16. Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
17. Bogdan, K. W. Synth. Commun. 1993, 23, 2481.
18. Aesa, M. C.; Baan, G.; Novak, L.; Szantay, C. Synth. Commun. 1995, 25, 2575.
19. Iranpoor, N.; Firouzabadi, H.; Aghapour, Gh.; Vaez zadeh, A. R. Tetrahedron 2002, 58, 8689.
20. (a) Wang, W.; Li, Y.; Attardo, G. J. Org. Chem. 1997, 62, 6598.
21. (b) Becker, H. D.; Bjork, A.; Adler, E. J. Org. Chem. 1980, 45, 1596.