P(RNCH2CH2)3N-catalyzed α,β-dimerization of unsaturated nitriles: Formation of 2-alkylidene-3-alkylglutaronitriles

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 10057-10059

  Kisanga, Philip ^a   D'Sa, Bosco ^a   Verkade, John ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NITRILE;

ARTICLE; CATALYSIS; DIMERIZATION; SYNTHESIS;

EID: 0032567308     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981513f     Document Type: Article

References (16)

1. Baizer, M.; Anderson, J. D. J. Org. Chem. 1965, 30, 1357.
2. Baizer, M.; Chruma, L.; White, A. Tetrahedron Lett. 1973, 52, 5209.
3. Misorro, A.; Uchida, Y.; Tamai, K.; Hidai, M. Bull. Chem. Soc. Jpn. 1967, 40, 931.
4. Saegusa, T.; Ito, Y.; Tomita, S.; Kinoshita, H. J. Org. Chem. 1970, 35, 670.
5. Saegusa, T.; Ito, Y.; Tomita, S. J. Am. Chem. Soc. 1971, 93, 5656.
6. Saegusa, T.; Ito, Y.; Tomita, S. Bull. Chem. Soc. Jpn. 1972, 45, 830.
7. White, A.; Baizer, M. M. J. Chem. Soc., Perkins Trans, 1 1973, 2231.
8. Shabtai, J.; Ney-Igner, E.; Pines, H. J. Org. Chem. 1975, 40, 1158.
9. Dewael, A. Bull. Soc. Chim. Belg. 1932, 324.
10. Schmidt, H.; Lensink, C.; Xi, S. K.; Verkade, J. G. Z. Anorg. Allg. Chem. 1989, 578, 75.
11. D'Sa, B.; Verkade, J. G. Phosphrus, Sulfur Silicon Relat. Elem. 1997, 123, 301.
12. Wroblewski, A. E.; Pinkas, J.; Verkade, J. G. Main Group Chem. 1995, 1, 69.
13. D'Sa, B.; Kisanga, P.; Verkade, J. G. J. Org. Chem. 1998, 63, 3961.
14. Kisanga, P.; McLeod, D.; D'Sa, B.; Verkade, J. G. In press.
15. Palomo, C.; Aizpuruo, J.; Garcia, J.; Ganboa, I.; Cossio, F. B.; Leua, B.; Lopez, C. J. Org. Chem. 1990, 55, 2498.
16. See Supporting Information for spectral data recorded for these compounds.