Organic syntheses via transition metal complexes, 98 unprecedented rearrangement of (1,3-butadien-2-yl)carbene into (1,3-butadien-1-yl)carbene complexes (M = Cr, W)

Synlett

Volumn , Issue 10, 1998, Pages 1120-1122

  Aumann, Rudolf ^a   Kößmeier, Michael ^a   Jäntti, Anu ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28144451022     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1861     Document Type: Article

References (21)

1. Preceeding paper in this series: Aumann, R.; Yu, Z.; Fröhlich, R. Eur. J. Inorg. Chem. 1998, in print.
2. For recent reviews see: (a) de Meijere, A. Pure Appl. Chem. 1996, 68, 61.
3. (b) Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 161.
4. (a) Aumann, R.; Roths, K.; Grehl, M. Synlett 1993, 669.
5. (b) Aumann, R.; Kößmeier, M.; Roths, K.; Fröhlich, R. Synlett 1994, 1041.
6. (c) Meyer, A. G.; Aumann, R. Synlett 1995, 1011.
7. (d) Aumann, R.; Roths, K.; Jasper, B.; Fröhlich, R. Organometallics 1996, 15, 1257.
8. (e) Aumann, R.; Kößmeier, M.; Zippel, F. Synlett 1997, 621.
9. (f) Yu, Z.; Aumann, R.; Fröhlich, R.; Roths, K.; Hecht, J. J. Organomet. Chem. 1997, 541, 187.
10. (g) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018.
11. (a) Aumann, R.; Roths, K.; Läge, M.; Krebs, B. Synlett 1993, 667.
12. (b) Aumann, R.; Roths, K.; Fröhlich, R. Organometallics 1997, 16, 5893.
13. 2), 2.06 and 1.85 (1:1 H, m each, diastereotopic
14. An (electrocyclic) conversion of simple organic 4-aminocyclobutenes to 1-aminobuta-1,3-dienes has been described, e.g., by Brannock, K. C.; Burpitt, R. D.; Goodlett, V. W.; Thweat, J. G. J. Org. Chem. 1964, 29, 818.
15. An amine catalyzed ring opening of 4-aminocyclobutenes to 1-aminobuta-1,3-dienes involving a migration of the amino group was studied by Egberink, R. J. M; Verboom, W.; Benders, P. H.; Harkema, S.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1988, 107, 388. The regiochemistry of the latter rearrangement is different from that of a carbene complex A to a 1-metallatriene 4 as outlined in Scheme 1.
16. Aumann, R.; Hildmann, B.; Fröhlich, R. J. Organomet. Chem. 1998, 17, 1197.
17. 2 each, C7 and C8).
18. Crystal structure analysis of 7 by Anu Jäntti, Münster. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-102593. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44 (1223)336033, e-mail: deposit@ccdc.cam.ac.uk].
19. Fischer, E.O.; Schubert, U.; Kleine, W.; Fischer, H. Inorganic Synthesis 1979, 19, 164.
20. Prepared according to the procedure given by (a) Carlson, R.; Nilson, Å. Acta Chemica Scandinavica B 1984, 38, 49.
21. (b) Azzaro, M.; Geribaldi, S.; Videau, B. Synthesis 1981, 880.