N-CN bond cleavage of cyanamides by a transition-metal complex

Journal of the American Chemical Society

Volumn 131, Issue 1, 2009, Pages 38-39

  Fukumoto, Kozo ^a   Oya, Tsukuru ^a   Itazaki, Masumi ^a   Nakazawa, Hiroshi ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BOND CLEAVAGES; IRON COMPLEX; MOLYBDENUM COMPLEX; ROOM TEMPERATURE; SILYL-MIGRATION; THERMAL CONDITION; TRANSITION-METAL COMPLEX;

IRON ANALYSIS; METAL COMPLEXES; MOLYBDENUM; MOLYBDENUM COMPOUNDS; SILANES; TRANSITION METALS;

IRON COMPOUNDS;

AMIDINE; BENZENE; BORANE DERIVATIVE; CARBON; CYANAMIDE; DIMETHYLCYANAMIDE; HYDROGEN; IRON COMPLEX; ISOCYANATE; MERCURY; METAL COMPLEX; MOLYBDENUM COMPLEX; NITRILE; NITROGEN; ORGANIC COMPOUND; OXYGEN; SILICON; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHEMOSENSITIZATION; COMPLEX FORMATION; CYCLOADDITION; ELECTRON; ENERGY YIELD; HEATING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE TRANSITION; PHOTOREACTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; SILYLATION; STEREOCHEMISTRY; SYNTHESIS; THERMAL ANALYSIS;

EID: 67849121016     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807896b     Document Type: Article

References (28)

1. See, for example: (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770.
2. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698-1712.
3. (c) Naota, T.; Takaya, H.; Murabashi, S. I. Chem. Rev. 1998, 98. 2599-2660.
4. (d) Zhang, Y.; Li, C.-J. Angew. Chem., Int. Ed. 2006, 45, 1949-1952.
5. (e) Ma, K.; Piers, W. E.; Parvez, M. J. Am. Chem. Soc. 2006, 128, 3303-3312.
6. (f) Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698-1699.
7. (g) Goosen, L. J. Angew. Chem., Int. Ed 2002, 41, 3775-3778.
8. (h) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154-162.
9. (i) Crabtree, R. H. J. Organomet. Chem. 2004, 689, 4083-4091.
10. See for example: (a) Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610-618.
11. (b) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870-883.
12. (c) Storsberg, J.; Yao, M.-L.; Ocal, N.; De Meijere, A.; Adam, A. E. W.; Kaufmann, D. E. Chem. Commun. 2005, 5665-5666.
13. (d) Nakazawa, H.; Kawasaki, T.; Miyoshi, K.; Suresh, C. H.; Koga, N. Organometallics 2004, 23, 117-126.
14. (e) Chianese, A. R.; Zeglis, B. M.; Crabtree, R. H. Chem. Commun. 2004, 2176-2177.
15. (f) Terao, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2001, 123, 10407-10408.
16. (a) Lei, Y.; Wrobleski, A. D.; Golden, J. E.; Powell, D. R.; Aube, J. J. Am. Chem. Soc. 2005,127, 4552-4553.
17. (b) Fran, L.; Yang, L.; Guo, C.; Foxman, B. M.; Ozerov, O. V. Organometallics 2004, 23, 4778-4787.
18. (c) Yao, M.-L.; Adiwidjaja, G.; Kanfmann, D. E. Angew. Chem., Int. Ed. 2002, 41, 3375-3378.
19. (d) Niklas, N.; Heinemann, F. W.; Hampel, F.; Alsfasser, R. Angew. Chem., Int. Ed. 2002, 41, 3386-3388.
20. See for example: (a) Maercker, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 972-989.
21. (b) Kabalka, G. W.; Yao, M.-L.; Borella, S.; Goins, L. K. Organometallics 2007, 26, 4112-4114.
22. (c) Szu, P.-h.; He, X.; Zhao, L.; Liu, H.-w. Angew. Chem., Int. Ed 2005, 44, 6742-6746. (d) Casado, F.; Pisano, L.; Farriol, M.; Gallardo, I.; Marquet, J.; Melloni, G. J. Org. Chem. 2000, 65, 322-331.
23. Cunningham, I. D.; Light, M. E.; Hursthouse, M. B. Acat Crystallogr., Sect. C: Cryst. Struct. Commun. 1999, 55, 1833-1835.
24. Vliet, E. B. Org Synth. 1941, 1, 201-202.
25. Syntheses of boran adduct of cyanamide and confirmation of the adduct at the amino nitrogen have been reported: Henneike, H. F.; Drago, R. S. Inorg. Chem. 1968, 7, 1908-1915.
26. Selected bond lengths (A) and angles (deg): C2-N1, 1.327(3); C2-N2, 1.303(2); C3-N1, 1.455(3); C4-N1, 1.458(3); C2-N1-C3, 123.4(2); C2-N1-C4, 119.5(2); C3-N1-C4, 117.0(2); Fe1-C2-N1, 149.40(17); Fe1-C2-N2, 78.31(15); N1-C2-N2, 132.3(3); Fe1-N2-Si1, 134.04(12); Fe1-N2-C2, 63.04(13); Si1-N2-C2, 141.24(19).
27. (a) Nakazawa, H.; Kamata, K.; Itazaki, M. Chem. Commun. 2005, 4004-4006.
28. (b) Nakazawa, H.; Itazaki, M.; Kamata, K.; Ueda, K. Chem.-Asian J. 2007, 2, 882-888.