A general one-step synthesis of β-nitronitriles

Organic Letters

Volumn 10, Issue 18, 2008, Pages 4141-4143

  Anderson, James C ^a   Blake, Alexander J ^a   Mills, Matthew ^a   Ratcliffe, Paul D ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CYANIDE; NITRILE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALKENES; CYANIDES; NITRILES;

EID: 55949092663     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801691c     Document Type: Article

References (17)

1. Calderari, G.; Seebach, D. Helv. Chim. Acta 1995, 68, 1592.
2. Pinnick, H. W. Org. React. 1990, 38, 655.
3. Larock, R. C. Comprehensive Organic Transformations; Wiley-VCH: New York, 1989; p 411.
4. Tamura, R.; Kamimura, A.; Ono, N. Synthesis 1991, 423.
5. Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Chem. 2002, 1877.
6. Lassaletta, J. M.; Fernández, R.; Gasch, C.; Vázquez, J. Tetrahedron 1996, 52, 9143.
7. Ros, F.; Rosa, J. J. Org. Chem. 1988, 53, 2868.
8. (a) Cook, F. C.; Bowers, C. W.; Liotta, C. L. J. Org. Chem. 1974, 39, 3416.
9. (b) Liotta, C. L.; Dabdoub, A. M.; Zalkow, L. H. Tetrahedron Lett. 1977, 18, 1117.
10. Fieser, L. F.; Gates, M. J. Am. Chem. Soc. 1946, 68, 2249.
11. Melton, J.; McMurry, J. E. J. Org. Chem. 1975, 40, 2138.
12. A similar dimer from entry l was isolated in 3% yield from a 3.5 mmol scale reaction.
13. Singh, V. S.; Gupta, S. M. L. Curr. Sci. 1981, 50, 816.
14. Sakakibara, T.; Ikeda, Y.; Sudoh, R. Bull. Chem. Soc. Jpn. 1982, 55, 635.
15. Values of CN = 0.84 kJ/mol: (a) Jensen, F. R.; Bushweller, C. H.; Beck, B. H. J. Am. Chem. Soc. 1969, 97,
16. 3 = 7.28 kJ/mol: Booth, H.; Everett, J. R. J. Chem. Soc., Perkin 2 1980, 255.
17. McMurry, J. E.; Melton, J. J. Org. Chem. 1973, 38, 4367.