Generation and Trapping Reactions of a Formal 1:1 Complex between Singlet Carbon and 2,2′-Bipyridine

Angewandte Chemie - International Edition

Volumn 37, Issue 3, 1998, Pages 344-347

  Weiss, Robert ^a   Reichel, Silvia ^a   Handke, Matthias ^a   Hampel, Frank ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Carbones; Diazo compounds; Hybridization; Imidazolylidenes

Indexed keywords

2,2' BIPYRIDINE; CARBON; DEPROTONATION; HYBRIDIZATION; SINGLET CARBON;

EID: 0032536395     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980216)37:3<344::AID-ANIE344>3.0.CO;2-H     Document Type: Article

References (24)

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5. R. Weiss, J. Seubert, F. Hampel, Angew. Chem. 1994, 106, 2038; Angew. Chem. Int. Ed. Engl. 1994, 33, 1952.
6. An analogous fragmentation of a triphenylphosphonio-substituted diazoacetic ester was already reported; M. Regitz, A. E. M. Tawfik, H. Heydt. Liebigs Ann. Chem. 1981, 1865.
7. a) R. Weiss, M. Handke, S. Reichel, F. Hampel, unpublished results;
8. b) see also R. Weiss, R. Roth, Synthesis 1987, 870.
9. This salt had already been synthesized in low yield (25%) by an alternative method: I. C. Calder, W. H. F. Sasse, Aust. J. Chem. 1965, 18, 1819.
10. [15]
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16. 13C) = 127: T. A. Taton, P. Chen; Angew. Chem. 1996, 108, 1098; Angew. Chem. Int. Ed. Engl. 1996, 55, 1011.
17. S. Reichel, Dissertation. Universität Erlangen-Nürnberg, planned in 1998.
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19. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100542. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: int. code + (44)1223-336033; e-mail: deposit@ccdc.cam.ac.uk).
20. N,N′-Dimethylselenourea: C-Se 1.866, C(Se)-N 1.32 Å: H. M. K. K. Pathirana, T. J. Weiss, J. H. Reibeneis, R. A. Zingaro, E. A. Meyers, Z. Kristallogr. 1994, 209, 697.
21. With the length of the [0] bridge between the six-membered rings, calculated with ab initio methods, as an indicator: 3: 1.461, 4: 1.379, 5: 1-353 Å.
22. H. Schmidbaur, Angew. Chem. 1983, 95, 980; Angew. Chem. Int. Ed. Engl. 1983, 22, 907.
23. H. Schmidbaur, Angew. Chem. 1983, 95, 980; Angew. Chem. Int. Ed. Engl. 1983, 22, 907.
24. We will report on compounds of this type separately.