Synthesis of the adduct DMAP·BrP(=N-Mes)2 and of the salt [ (DMAP)2P (=NMes)2]+Br

Angewandte Chemie - International Edition

Volumn 39, Issue 15, 2000, Pages 2768-2771

  Blättner, Markus ^a   Nieger, Martin ^a   Ruban, Alexander ^a   Schoeller, Wolfgang W ^b   Niecke, Edgar ^a  

^a UNIVERSITY OF BONN   (Germany)

^b BIELEFELD UNIVERSITY   (Germany)

Author keywords

Ab initio calculations; Iminophosphoranes; Phosphorus

Indexed keywords

ALLENE DERIVATIVE; CATION; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; HYBRIDIZATION; MOLECULAR STABILITY; QUANTUM MECHANICS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0040778475     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000804)39:15<2768::AID-ANIE2768>3.0.CO;2-4     Document Type: Article

References (28)

1. "The Chemistry of Ketenes, Allenes, and Related Compounds"; The Chemistry of Functional Groups (Ed.: S. Patai), Wiley, New York, 1980.
2. See for example: a) W. Kutzelnigg, Angew. Chem. 1984, 96, 262-286; Angew. Chem. Int. Ed. Engl. 1984, 23, 272-296;
3. See for example: a) W. Kutzelnigg, Angew. Chem. 1984, 96, 262-286; Angew. Chem. Int. Ed. Engl. 1984, 23, 272-296;
4. b) "Bonding Properties of Low Coordinated Phosphorus Compounds": W. W. Schoeller in Multiple Bonding and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz, O. J. Scherer). Thieme, Stuttgart, 1989, pp. 5-32.
5. [4] however, they are extended π systems.
6. K. Dimroth, P. Hoffmann, Angew. Chem. 1964, 76, 433; Angew. Chem. Int. Ed. Engl. 1964, 3, 379.
7. K. Dimroth, P. Hoffmann, Angew. Chem. 1964, 76, 433; Angew. Chem. Int. Ed. Engl. 1964, 3, 379.
8. W. W. Schoeller, W. Haug, J. Strutwolf, T. Busch, J. Chem. Soc. Faraday Trans. 1996, 92, 1751-1755.
9. ∝ level is as follows: P -O 1.467 Å, O-P-O 180 . For the corresponding radical see: a) C. Xu, E. de Beer, D. M. Neumark, J. Chem. Phys. 1996, 104, 2749-2751; b) Z.-L. Lai, G. Hirsch, R. J. Buenker, Chem. Phys. Lett. 1996, 225, 350-356.
10. ∝ level is as follows: P -O 1.467 Å, O-P-O 180 . For the corresponding radical see: a) C. Xu, E. de Beer, D. M. Neumark, J. Chem. Phys. 1996, 104, 2749-2751; b) Z.-L. Lai, G. Hirsch, R. J. Buenker, Chem. Phys. Lett. 1996, 225, 350-356.
11. 1: M. Meisel, P. Lönnecke, A. R. Grimmer, D. Wulff- Molden, Angew. Chem. 1997, 109, 1940-1942; Angew. Chem. Int. Ed. Engl. 1997, 36, 1869-1870.
12. 1: M. Meisel, P. Lönnecke, A. R. Grimmer, D. Wulff- Molden, Angew. Chem. 1997, 109, 1940-1942; Angew. Chem. Int. Ed. Engl. 1997, 36, 1869-1870.
13. 1: M. Meisel, P. Lönnecke, A. R. Grimmer, D. Wulff-Molden, Angew. Chem. 1997, 109, 1940-1942; Angew. Chem. Int. Ed. Engl. 1997, 36, 1869-1870.
14. 1: M. Meisel, P. Lönnecke, A. R. Grimmer, D. Wulff- Molden, Angew. Chem. 1997, 109, 1940-1942; Angew. Chem. Int. Ed. Engl. 1997, 36, 1869-1870.
15. A. Ruban, M. Nieger, E. Niecke, Angew. Chem. 1993, 105, 1544-1545; Angew. Chem. Int. Ed. Engl. 1993, 32, 1419-1420.
16. A. Ruban, M. Nieger, E. Niecke, Angew. Chem. 1993, 105, 1544- 1545; Angew. Chem. Int. Ed. Engl. 1993, 32, 1419-1420.
17. "Bis(imino)phosphoranes": E. Niecke, D. Gudat in Multiple Bonding and Low Coordination in Phosphorus Chemistry (Eds.: M. Regitz, O. J. Scherer), Thieme, Stuttgart, 1990, pp. 392-404.
18. 2) was 0.2540, with a conventional R(F)=0.0780 for 545 parameters and 91 restraints. One p-tBu group and the triflate are disordered. 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-132812 (2), CCDC-132813 (3 · Br), and CCDC-132814 (4·TfO). Copies of the data can be obtained free of charge on application to CCDC. 12 Union Road, Cambridge CB21EZ, UK (fax: (+ 44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
19. G. M. Sheldrick, SHELXS-86, Acta Crystallogr. Sect. A 1990, 46, 467-473.
20. G. M. Sheldrick, SHELXL-93, University of Göttingen, 1993.
21. N. Walker, D. Stuart, Acta Crystallogr. Sect. A 1983, 39, 158-166.
22. S. Pohl, B. Krebs, E. Niecke, Angew. Chem. 1975, 87, 284-285; Angew. Chem. Int. Ed. Engl. 1975, 14, 261-262.
23. S. Pohl, B. Krebs, E. Niecke, Angew. Chem. 1975, 87, 284-285; Angew. Chem. Int. Ed. Engl. 1975, 14, 261-262.
24. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, B. G. M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Avala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gom-perts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian 94 (Revision A.1), Gaussian, Inc., Pittsburgh, PA. 1995.
25. Calculated at the CCSD(t)/6-31g*//MP2(fc)/6-31g* level with zero-point vibrational energy correction at the MP2(fc) level.
26. R. F. W. Bader, Atoms in Molecules: A Quantum Theory, Oxford University Press, Oxford, 1990.
27. V. Romanenko, M. Sanchez, Coord. Chem. Rev. 1997, 158, 275-324.
28. 3SO3] : P-N(Mes*) 153.5(5), P-N(H, Mes*) 162.7(5), P-N(heterocycle) 174.4(5), P-C 188.3(6) pm.