Mesoionic carbenes: Reactions of 1, 3-diphenyltetrazol-5-ylidene with electron-deficient alkenes, and synthesis and catalytic activities of the (tetrazol-5-ylidene)rhodium(I) complexes

Journal of Heterocyclic Chemistry

Volumn 46, Issue 2, 2009, Pages 164-171

  Araki, Shuki ^a   Yokoi, Keisaku ^a   Sato, Ryosuke ^a   Hirashita, Tsunehisa ^a   Setsune, Jun Ichiro ^b  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

^b KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIPHENYLTETRAZOL 5 YLIDENE; ALKENE DERIVATIVE; AMPHOLYTE; CARBENOID; ELECTROPHILE; HYDRAZINE DERIVATIVE; RHODIUM COMPLEX; TETRACYANOETHYLENE; TETRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEGRADATION; ELECTRON; MICHAEL ADDITION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 65349111835     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.61     Document Type: Article

References (28)

1. (a) Arduengo, A. J.; Harlow, R. L.; Kline, M. J Am Chem Soc 1991, 113, 361;
2. (b) Arduengo, A. J. Acc Chem Res 1999, 32, 913;
3. Alder, R. W.; Blake, M. E.; Chaker, L.; Narvey, J. N.; Paolini, F.; Schnuetz, J. Angew Chem Int Eng 2004, 43, 5896.
4. (a) Ohta, M.; Kato, H. In Nonbenzenoid Aromatics I; Snyder, J. P., Ed.;Academic Press: New York, 1969, p 117;
5. (b) Ollis, W. D.; Ramsden, C. A. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York, 1976; Vol. 19, p 1;
6. Newton, C. G.; Ramsden, C. A. Tetrahedron, 1982, 38, 2965;
7. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123.
8. Norris, W. P.; Henry, R. A. Tetrahedron Lett 1965, 1213.
9. Araki, S.; Wanibe, Y.; Uno, F.; Morikawa, A.; Yamamoto, K.; Chiba, K.; Butsugan, Y. Chem Ber 1993, 126, 1149.
10. Araki, S.; Yamamoto, K.; Yagi, M.; Inoue, T.; Fukagawa, H.; Hattori, H.; Yamamura, H.; Kawai, M.; Butsugan, Y. Eur J Org Chem 1998, 121.
11. The structure of 3 was previously reported errornously as 1-cyano-1, 3-diphenyltriazene [4].
12. Lowack, R. H.; Weiss, R. J Am Chem Soc 1990, 112, 333.
13. Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Liebigs Ann Chem 1996, 2019.
14. For other 5-tetrazoliomethylides; see: (a) Araki, S.; Mizuya, J.; Butsugan, Y. J Chem Soc Perkin Trans1, 1985, 2439;
15. (b) Araki, S.; Kuzuya, M.; Hamada, K.; Nogura, M.; Ohata, N. Org Biomol Chem 2003, 1, 978.
16. (a) Rieker, A. Inst Chim Belge 1971, 36, 1078;
17. (b) Cadogan, J. I. G.; Murray, C. D.; Sharp, J. T. J Chem Soc 1973, 16, 572.
18. Herrmann, W. A.; Elison, M.; Fischer, J.; Köcher, C.; Artus, G. R. J. Chem Eur J 1996, 2, 772.
19. (a) Ender, D.; Gielen, H. J Organomet Chem 2001, 70, 617;
20. (b) Buron, C.; Stelzig, L.; Guerret, O.; Gornitzka, H.; Romanenko, V.; Bertrand, G. J Organomet Chem 2002, 640, 70.
21. (a) Herrmann, W. A.; Köcher, C. Angew Chem Int Ed Engl 1997, 36, 2162;
22. (b) Herrmann, W. A. Angew Chem Int Ed Engl 2002, 41, 1290;
23. Trnka, T. M.; Grubbs, R. H. Acc Chem Res 2001, 34, 18.
24. Kokubo, K.; Matsumasa, K.; Miura, M.; Momura, M. J Org Chem 1996, 61, 6941.
25. Iqbal, A. F. M. Angew Chem Int Ed Eng 1972, 11, 634.
26. Bestmann, H. J.; Schade, G.; Luetke, H.; Möbius, T. Chem Ber 1985, 118, 2640.
27. Simig, G.; Lempert, K.; Tomas, J.; Czira, G. Tetrahedron, 1975, 31, 1195.
28. Fitzgerald, J.; Taylor, W.; Owen, H. Synthesis, 1991, 686.