Formation of n-butyldiazoate by reaction of [M(CN)5NO]2- (M = Fe, Ru, Os) with lithium n-butylamide

Organometallics

Volumn 21, Issue 10, 2002, Pages 2021-2023

  Trápani, Cecilia ^a   Escola, Natalia ^a   Doctorovich, Fabio ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOPHILIC ATTACKS;

CONCENTRATION (PROCESS); FOURIER TRANSFORM INFRARED SPECTROSCOPY; LITHIUM COMPOUNDS; MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE EQUILIBRIA; STOICHIOMETRY; ULTRAVIOLET SPECTROSCOPY;

ORGANOMETALLICS;

EID: 0038451524     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om011026h     Document Type: Article

References (14)

1. Bowden, W. L.; Little, W. F.; Meyer, T. J. J. Am. Chem. Soc. 1977, 99, 4340.
2. Doctorovich, F.; Trápani, C. Tetrahedron Lett. 1999, 40, 4635.
3. Doctorovich, F.; Escola, N.; Trápani, C.; Estrin, D. A.; Turjanski, A. G.; González Lebrero, M. C. Organometallics 2000, 19, 3810.
4. Doctorovich, F.; Granara, M.; Di Salvo, F., Transition Met. Chem. 2001, 26, 505.
5. Di Salvo, F.; Crespo, A.; Escola, N.; Estrin, D. A.; Doctorovich, F. Tetrahedron, in press.
6. 8 was added to a 2 M pyridine solution of the corresponding complex and allowed to react at 0 °C protected from light. The reaction was instantaneous, as judged by the color change. The complex to amide ratios studied ranged from 1:0.2 to 1:4.
7. Aubrecht, K. B.; Lucht, B. L.; Collum, D. B. Organometallics 1999, 18, 2981.
8. Watson, S. C.; Eastham, J. F. J. Organomet. Chew., 1967, 9, 165.
9. 13C NMR shifts are slightly different due to the change in solvent and counterion. Several unsuccessful attempts were made to dissolve the independently prepared sodium (E)-n-butyldiazoate in a THF - pyridine mixture with/without the addition of tetrabutylammonium salts or crown ethers. Presumably, the (E)-n-butyldiazoate formed in the reaction is kept in solution by the presence of the tetrabutylammonium counterion.
10. Thiele, J. Chem. Ber. 1908, 41, 2806.
11. Baraldo, L. M.; Forlano, P.; Parise, A. R.; Slep, L.; Olabe, J. A. Coord. Chem. Rev. 2001, 219-221, 881.
12. Ho, J.; Fishbein, J. C. J. Am. Chem. Soc. 1994, 116, 6611.
13. Lown, J. W.; Chauhan, S. M. S.; Koganty, R. R.; Sapse A.-N. J. Am. Chem. Soc. 1984, 106, 6401.
14. 12