Isolation and reaction of (indolin-3-ylidene)pentacarbonyltungsten generated from tungsten-containing azomethine ylide

Chemistry Letters

Volumn 33, Issue 1, 2004, Pages 16-17

  Takaya, Jun ^a   Kusama, Hiroyuki ^a   Iwasawa, Nobuharu ^a  

^a Tokyo Institute of Technology ^*  (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

(INDOLIN 3 YLIDENE)PENTACARBONYLTUNGSTEN; CARBENOID; CARBONYL DERIVATIVE; ETHER DERIVATIVE; IMINE; METAL COMPLEX; TUNGSTEN DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; LIGHT; PHOTOREACTIVITY; SPECTROSCOPY;

EID: 1342284726     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.16     Document Type: Article

References (20)

1. a) F. Z. Dörwald, "Metal Carbenes in Organic Synthesis," Wiley-VCH, Weinheim (1999)
2. b) M. J. Winter, in "Comprehensive Organometallic Chemistry II," ed. by E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon, New York (1995), Vol. 5, pp 172-192.
3. M. J. Winter, in "Comprehensive Organometallic Chemistry II," ed. by E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon, New York (1995), Vol. 5, pp 168-172. See also ref 1a.
4. Examples for the catalytic process including a non-heteroatom-stabilized carbene complex as the key intermediate, see; a) N. Iwasawa, M. Shido, and H. Kusama, J. Am. Chem. Soc., 123, 5814 (2001). b) K. Miki, F. Nishino, K. Ohe, and S. Uemura, J. Am. Chem. Soc., 124, 5260 (2002).
5. Examples for the catalytic process including a non-heteroatom-stabilized carbene complex as the key intermediate, see; a) N. Iwasawa, M. Shido, and H. Kusama, J. Am. Chem. Soc., 123, 5814 (2001). b) K. Miki, F. Nishino, K. Ohe, and S. Uemura, J. Am. Chem. Soc., 124, 5260 (2002).
6. Alkyl carbene derivatives, especially those having an α-hydrogen, are highly reactive to give 1,2-hydrogen migration products, a) C. P. Casey, L. D. Albin, and T. J. Burkhardt, J. Am. Chem. Soc., 99, 2533 (1977). b) J. Barluenga, A. Ballesteros, R. de la R. Bernardo, J. Santamaria, E. Rubio, and M. Tomas, J. Am. Chem. Soc., 125, 1834 (2003).
7. Alkyl carbene derivatives, especially those having an α-hydrogen, are highly reactive to give 1,2-hydrogen migration products, a) C. P. Casey, L. D. Albin, and T. J. Burkhardt, J. Am. Chem. Soc., 99, 2533 (1977). b) J. Barluenga, A. Ballesteros, R. de la R. Bernardo, J. Santamaria, E. Rubio, and M. Tomas, J. Am. Chem. Soc., 125, 1834 (2003).
8. There are several reports on the synthesis and isolation of diarylcarbene complexes, a) C. P. Casey, T. J. Burkhardt, and C. A. Bunnell, J. Am. Chem. Soc., 99, 2127 (1977). b) K. H. Dötz and J. Preiffer, Chem. Commun., 1996, 895. Other examples for the isolation of non-heteroatom-stabilized carbene complexes, see; c) H. Fischer, S. Zeuner, and K. Ackermann, J. Chem. Soc., Chem. Commun., 1984, 684. d) K. Miki, T. Yokoi, F. Nishino, K. Ohe, and S. Uemura, J. Organomet. Chem., 645, 228 (2002).
9. There are several reports on the synthesis and isolation of diarylcarbene complexes, a) C. P. Casey, T. J. Burkhardt, and C. A. Bunnell, J. Am. Chem. Soc., 99, 2127 (1977). b) K. H. Dötz and J. Preiffer, Chem. Commun., 1996, 895. Other examples for the isolation of non-heteroatom-stabilized carbene complexes, see; c) H. Fischer, S. Zeuner, and K. Ackermann, J. Chem. Soc., Chem. Commun., 1984, 684. d) K. Miki, T. Yokoi, F. Nishino, K. Ohe, and S. Uemura, J. Organomet. Chem., 645, 228 (2002).
10. There are several reports on the synthesis and isolation of diarylcarbene complexes, a) C. P. Casey, T. J. Burkhardt, and C. A. Bunnell, J. Am. Chem. Soc., 99, 2127 (1977). b) K. H. Dötz and J. Preiffer, Chem. Commun., 1996, 895. Other examples for the isolation of non-heteroatom-stabilized carbene complexes, see; c) H. Fischer, S. Zeuner, and K. Ackermann, J. Chem. Soc., Chem. Commun., 1984, 684. d) K. Miki, T. Yokoi, F. Nishino, K. Ohe, and S. Uemura, J. Organomet. Chem., 645, 228 (2002).
11. There are several reports on the synthesis and isolation of diarylcarbene complexes, a) C. P. Casey, T. J. Burkhardt, and C. A. Bunnell, J. Am. Chem. Soc., 99, 2127 (1977). b) K. H. Dötz and J. Preiffer, Chem. Commun., 1996, 895. Other examples for the isolation of non-heteroatom-stabilized carbene complexes, see; c) H. Fischer, S. Zeuner, and K. Ackermann, J. Chem. Soc., Chem. Commun., 1984, 684. d) K. Miki, T. Yokoi, F. Nishino, K. Ohe, and S. Uemura, J. Organomet. Chem., 645, 228 (2002).
12. H. Kusama, J. Takaya, and N. Iwasawa, J. Am. Chem. Soc., 124, 11592 (2002).
13. 6W: C, 50.41; H, 3.92; N, 2.18. Found: C, 50.67; H, 4.12; N, 2.13.
14. See Ref 1a, 4b, 5c.
15. There are few reports on the synthesis and isolation of alkylcarbene complexes of group 6 metal pentacarbonyl; see for examples; a) J. Preiffer and K. H. Dötz, Organometallics, 17, 1353 (1998). b) K. H. Dötz, M. Papall, G. Müller, and K. Ackermann, J. Organomet. Chem., 383, 93 (1990).
16. There are few reports on the synthesis and isolation of alkylcarbene complexes of group 6 metal pentacarbonyl; see for examples; a) J. Preiffer and K. H. Dötz, Organometallics, 17, 1353 (1998). b) K. H. Dötz, M. Papall, G. Müller, and K. Ackermann, J. Organomet. Chem., 383, 93 (1990).
17. NOEs were observed between the methyl group and o-proton of the phenyl substituent and between the methyl group and the methin proton on the t-BuO-substituted carbon.
18. 1,2-Alkyl migration of group 6 metal carbene intermediates is reported in a few, specific cases. See; a) M. Zora, J. W. Herndon, Y. Li, and J. Rossi, Tetrahedron, 57, 5097 (2001). b) K. Nagao, M. Chiba, and S.-W. Kim, Synthesis, 1983, 197.
19. 1,2-Alkyl migration of group 6 metal carbene intermediates is reported in a few, specific cases. See; a) M. Zora, J. W. Herndon, Y. Li, and J. Rossi, Tetrahedron, 57, 5097 (2001). b) K. Nagao, M. Chiba, and S.-W. Kim, Synthesis, 1983, 197.
20. No isomeric carbene complexes were observed during this NMR study.