Splitting a C-O bond in dialkylethers with bis(1,2,4-tri-tert- butylcyclopentadienyl)cerium hydride does not occur by a σ-bond metathesis pathway: A combined experimental and DFT computational study

New Journal of Chemistry

Volumn 34, Issue 10, 2010, Pages 2189-2196

  Werkema, Evan L ^a   Yahia, Ahmed ^b,c   Maron, Laurent ^b   Eisenstein, Odile ^d   Andersen, Richard A ^a  

^a LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^b UNIVERSITÉ DE TOULOUSE   (France)

^c DIF   (France)

^d UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ALKENE; ALKYL ETHER; ALKYL GROUP; BIS(1,2,4-TRI TERTBUTYLCYCLOPENTADIENYL)CERIUM HYDRIDE; BUTANE; CARBON; CERIUM; DEUTERIUM; ETHER; METHYL GROUP; OXYGEN; PROPANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; PRIORITY JOURNAL;

EID: 77957820315     PISSN: 11440546     EISSN: 13699261     Source Type: Journal    
DOI: 10.1039/c0nj00261e     Document Type: Article

References (32)

1. E. L. Werkema E. Messines L. Perrin L. Maron O. Eisenstein R. A. Andersen J. Am. Chem. Soc. 2005 127 7781
2. E. L. Werkema R. A. Andersen A. Yahia L. Maron O. Eisenstein Organometallics 2009 28 3173
3. P. L. Watson J. Chem. Soc., Chem. Commun. 1983 276
4. M. E. Thompson S. M. Baxter A. R. Bulls B. J. Berger M. C. Nolan B. D. Santarsierio W. P. Schaefer J. E. Bercaw J. Am. Chem. Soc. 1987 109 203
5. B.-J. Deelman M. Booji A. Meetsma J. H. Teuben H. Kooijman A. L. Spek Organometallics 1995 14 2306
6. W. J. Evans T. A. Ulibarri J. W. Ziller Organometallics 1991 10 134
7. E. L. Werkema L. Maron O. Eisenstein R. A. Andersen J. Am. Chem. Soc. 2007 129 2529
8. E. L. Werkema L. Maron O. Eisenstein R. A. Andersen J. Am. Chem. Soc. 2007 129 6662
9. E. L. Werkema R. A. Andersen L. Maron O. Eisenstein Dalton Trans. 2010 10.1039/b918103b
10. S. Niu M. B. Hall Chem. Rev. 2000 100 353
11. K. Ziegler H.-G. Gellert Justus Liebigs Ann. Chem. 1950 567 185
12. A. Maercker W. Demuth Angew. Chem., Int. Ed. Engl. 1973 12 75
13. A. Maercker W. Demuth Justus Liebigs Ann. Chem. 1977 1909
14. A. Maercker Angew. Chem., Int. Ed. Engl. 1987 26 972
15. J. Clayden S. A. Yasin New J. Chem. 2002 26 191
16. K. Tomooka, in The Chemistry of Organolithium Compounds Part 2, Patai Series: The Chemistry of Functional Groups, ed., Z. Rappoport, and, I. Marek, Wiley, New York, 2004, pp. 749-828
17. M. Braun, in The Chemistry of Organolithium Compounds Part 2, Patai Series: The Chemistry of Functional Groups, ed., Z. Rappoport, and, I. Marek, Wiley, New York, 2004, pp. 829-900
18. V. H. Gessner C. Strohmann J. Am. Chem. Soc. 2008 130 14412
19. C. A. Bradley L. F. Veiros D. Pun E. Lobkovsky I. Keresztes P. J. Chirik J. Am. Chem. Soc. 2006 128 16600
20. W. A. Nugent D. W. Ovenall S. J. Holmes Organometallics 1983 2 161
21. W. A. Nugent R. M. Zubyk Inorg. Chem. 1986 25 4604
22. L. Maron E. L. Werkema L. Perrin O. Eisenstein R. A. Andersen J. Am. Chem. Soc. 2005 127 279
23. A. Pierce, Silylation of Organic Compounds: A Technique for Gas-Phase Analysis, Pierce Chemical Company, Rockford, IL, 1968, pp. 18
24. M. Okazaki H. Tobita H. Ogino Chem. Lett. 1997 437
25. M. Dolg H. Stoll A. Savin H. Preuß Theor. Chim. Acta 1989 75 173
26. M. Dolg H. Stoll H. Preuß Theor. Chim. Acta 1993 85 441
27. L. Maron O. Eisenstein J. Phys. Chem. A 2000 104 7140
28. P. C. Hariharan J. A. Pople Theor. Chim. Acta 1973 28 213
29. J. J. P. Perdew Y. Wang Phys. Rev. B: Condens. Matter 1992 45 13244
30. A. D. Becke J. Chem. Phys. 1993 98 5648
31. K. Burke, J. P. Perdew and Y. Wang, in Electronic Density Functional Theory: Recent Progress and New Directions, ed., J. F. Dobson, G. Vignale, and, M. P. Das, Plenum Press, New York, 1998, pp. 81-111
32. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr. , T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, GAUSSIAN 03 (Revision C.02), Gaussian, Inc., Wallingford, CT, 2004