Nickel-catalyzed isomerization of 2-methyl-3-butenenitrile

Organometallics

Volumn 24, Issue 1, 2005, Pages 13-15

  Wilting, Jos ^a   Müller, Christian ^a   Hewat, Alison C ^a   Ellis, Dianne D ^b   Tooke, Duncan M ^b   Spek, Anthony L ^b   Vogt, Dieter ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ISOMERIZATION; MOLECULAR STRUCTURE; NICKEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS; X RAY CRYSTALLOGRAPHY;

CATALYTIC HYDROCYANATION; LIGAND PARAMETERS; OXIDATIVE ADDITION;

AROMATIC COMPOUNDS;

EID: 12344321479     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049206p     Document Type: Article

References (19)

1. Huthmacher, K.; Krill, S. Reactions with hydrogen cyanide (hydrocyanation). In Applied Homogeneous Catalysis with Organometallic Compounds; VCH: Weinheim, Germany, 1996; Vol. 1, pp 465486.
2. Goertz, W.; Kamer, P. C. J.; Van Leeuwen, P. W. N. M.; Vogt, D. Chem. Eur. J. 2001, 7(8), 1614-1618.
3. Tolman, C. A.; McKinney, R. J.; Seidel, W. C.; Druliner, J. D.; Stevens, W. R. Adv. Catal. 1985, 33, 1-46.
4. van der Vlugt, J. I.; Hewat, A. C.; Neto, S.; Sablong, R.; Mills, A. M.; Lutz, M.; Spek, A. L.; Mueller, C.; Vogt, D. Adv. Synth. Catal. 2004, 346(8), 993-1003.
5. Chaumonnot, A.; Lamy, F.; Sabo-Etienne, S.; Donnadieu, B.; Chaudret, B.; Barthelat, J. C.; Galland, J. C. Organometallics 2004, 23(14), 3363-3365.
6. Siegel, W. (BASF AG, 67063 Ludwigshafen, Germany) Ger. Offen. DE10150286, 2004.
7. Lenges, C. P. (E. I. Du Pont de Nemours & Co.) Phosphonite ligands and their use in hydrocyanation. WO03/076394, 2003.
8. Foo, T.; Garner, J. M.; Tam, W. (E. I. Du Pont de Nemours & Co., USA) Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles. WO99/06357, 1999.
9. Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116(22), 9869-9882.
10. Goertz, W.; Keim, W.; Vogt, D.; Englert, U.; Boele, M. D. K.; Van der Veen, L. A.; Kamer, P. C. J.; Van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1998(18), 2981-2988.
11. Vallee, C.; Valerio, C.; Chauvin, Y.; Niccolai, G. P.; Basset, J. M.; Santini, C. C.; Galland, J. C.; Didillon, B. J. Mol. Catal. A: Chem. 2004, 214(1), 71-81.
12. Tolman, C. A. Organometallics 1983, 2(5), 614-621.
13. The small sharp singlet at δ 23 ppm is an impurity.
14. Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35-68.
15. w = 0.0881); S = 1.03.
16. Brunkan, N. M.; Jones, W. D. J. Organomet. Chem. 2003, 683(1), 77-82.
17. 3 as the catalyst system in toluene and followed the product formation in time by GC. The results clearly showed zero-order kinetics.
18. McKinney, R. J.; Roe, D. C. J. Am. Chem. Soc. 1986, 107(1), 261-262.
19. Druliner, J. D. Organometallics 1984, 3(2), 205-208.