A stable tetraalkyl complex of nickel(IV)

Angewandte Chemie - International Edition

Volumn 48, Issue 2, 2009, Pages 290-294

  Carnes, Matthew ^a   Buccella, Daniela ^a   Chen, Judy Y C ^a   Ramirez, Arthur P ^b   Turro, Nicholas J ^a   Nuckolls, Colin ^a   Steigerwald, Michael ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b LGS Innovations   (United States)

Author keywords

Alkene ligands; Cycloaddition; Nickel; Organometallic compounds

Indexed keywords

BUTANE; LIGANDS; NICKEL ALLOYS; OLEFINS; ORGANIC COMPOUNDS; ORGANOMETALLICS;

A STABLES; ALKENE LIGANDS; ALKYL COMPLEXES; CYCLOBUTANE; LIGAND COUPLINGS; ORGANOMETALLIC COMPOUNDS; RING STRAINS;

NICKEL;

CYCLOOCTANE DERIVATIVE; LIGAND; NICKEL; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYCLIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; CYCLOOCTANES; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NICKEL; ORGANOMETALLIC COMPOUNDS;

EID: 58249110594     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804435     Document Type: Article

References (25)

1. M. Carnes, D. Buccella, J. Decatur, M. L. Steigerwald, C. Nuckolls, Angew. Chem. 2008, 120, 3024;
2. Angew. Chem. Int. Ed. 2008, 47, 2982.
3. a) P. Binger, Angew. Chem. 1972, 84, 352;
4. Angew. Chem. Int. Ed. Engl. 1972, 11, 309;
5. b) R. H. Grubbs, A. Miyashita, J. Am. Chem. Soc. 1978, 100, 7416;
6. c) P. W. Jolly, I. Tkatchenko, G. Wilke, Angew. Chem. 1971, 83, 329;
7. Angew. Chem. Int. Ed. Engl. 1971, 10, 329.
8. A. C. Cope, R. A. Pike, C. F. Spencer, J. Am. Chem. Soc. 1953, 75, 3212.
9. E. Niecke, J. F. Nixon, P. Wenderoth, B. F. Trigo Passos, M. Nieger, J. Chem. Soc. Chem. Commun. 1993, 10, 846.
10. 0(trans,trans,trans-cyclododecatriene)
11. (D. J. Brauer, C. Krüger, J. Organomet. Chem. 1972, 44, 397).
12. M. L. Steigerwald, W. A. Goddard, J. Am. Chem. Soc. 1985, 107, 5027.
13. a) P. W. Jolly, G. Wilke, The Organic Chemistry of Nickel, Vol. 1, Academic Press, New York, 1974;
14. b) P. W. Jolly, G. Wilke, The Organic Chemistry of Nickel, Vol. 2, Academic Press, New York, 1975.
15. 1H NMR spectroscopy. The conversion was complete after 30 min at 60°C in benzene. The solution turned dark red in color; however, no nickelaspirocyclononane 6 was observed, and we concluded that the color is a result of colloidal nickel.
16. [1] and the disclosure that it thermally forms cyclobutanes, others have verified this finding (J. Bornhoeft, J. Siegwarth, C. Nather, R. Herges, Eur. J. Org. Chem. 2008, 1619). Compound 3 is produced in minute amounts in these thermal reactions.
17. a) R. B. Woodward, R. Hoffman, The Conservation of Orbital Symmetry, VCH Publishers, New York, 1970;
18. b) R. H. Grubbs, A. Miyashita, M. Liu, P. Burk, J. Am. Chem. Soc. 1978, 100, 2418;
19. c) S. Takahashi, K. Suzuki, K. Sonogashira, N. Hagihara, J. Chem. Soc. Chem. Commun. 1976, 839.
20. M. J. Doyle, J. McMeeking, P. Binge, Chem. Commun. 1976, 376.
21. S. Takahashi, Y. Suzuki, N. Hagihara, Chem. Lett. 1974, 1363.
22. P. T. Matsunaga, J. C. Mavropoulos, G. L. Hillhouse, Polyhedron 1995, 14, 175.
23. In the spectrum, a new, broad signal appears around 3.5 ppm, which would be appropriate for benzylic protons.
24. A nickel atom with three alkyl substituents and a bromine atom attached: V. Dimitrov, A. Linden, Angew. Chem. 2003, 115, 2735;
25. Angew. Chem. Int. Ed. 2003, 42, 2631.