Van't Hoff-Le Bel stranger: Formation of a phosphonium cation with a planar tetracoordinate phosphorus atom

Angewandte Chemie - International Edition

Volumn 38, Issue 24, 1999, Pages 3677-3680

  Driess, Matthias ^a   Aust, Joachim ^a   Merz, Klaus ^a   Van Wüllen, Christoph ^a  

^a RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

Ab initio calculations; Phosphorus; Planarity; Zirconium

Indexed keywords

PHOSPHONIUM DERIVATIVE; PHOSPHORUS DERIVATIVE;

ARTICLE; CATION TRANSPORT; CHEMICAL STRUCTURE; GEOMETRY; ORGANIC CHEMISTRY; PREDICTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033576733     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991216)38:24<3677::AID-ANIE3677>3.0.CO;2-6     Document Type: Article

References (25)

1. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
2. a) J. H. van't Hoff, Arch. Neerl. Sci. Exactes. Nat. 1874, 9, 445;
3. b) J.-A. Le Bel, Bull. Soc. Chim. Fr. 1874, 22, 337.
4. T. A. Albright, J. K. Burdett, M.-H. Whangbo, Orbital Interactions in Chemistry, Wiley, New York, 1985.
5. R. Hoffmann, R. G. Adler, C. F. Wilcox, J. Am. Chem. Soc. 1970, 92, 4992.
6. R. Hoffmann, Pure Appl. Chem. 1971, 28, 181.
7. J. B. Collins, J. D. Dill, E. D. Jemmis, Y. Apeloig, P. von R. Schleyer, R. Seeger, J. A. Pople, J. Am. Chem. Soc. 1970, 98, 5419.
8. M.-B. Krogh-Jespersen, J. Chandrasekhar, E.-M. Würthwein, J. B. Collins, P. von R. Schleyer, J. Am. Chem. Soc. 1980, 102, 2263.
9. D. Röttger, G. Erker, Angew. Chem. 1997, 109, 841; Angew. Chem. Int. Ed. Engl. 1997, 36, 812, and references therein.
10. D. Röttger, G. Erker, Angew. Chem. 1997, 109, 841; Angew. Chem. Int. Ed. Engl. 1997, 36, 812, and references therein.
11. I. Hyla-Kryspin, R. Gleiter, M.-M. Rohmer, J. Devemy, A. Gundale, H. Pritzkow, W. Siebert, Chem. Eur. J. 1997, 3, 294.
12. E. Zeller, H. Beruda, A. Kolb, P. Bissinger, J. Riede, H. Schmidbaur, Nature 1991, 352, 141.
13. J. Li, P. Pyykkö, Inorg. Chem. 1993, 32, 2630.
14. A. Schmidpeter, S. Lochschmidt, Angew. Chem. 1986, 98, 271; Angew. Chem. Int. Ed. Engl. 1986, 25, 253.
15. A. Schmidpeter, S. Lochschmidt, Angew. Chem. 1986, 98, 271; Angew. Chem. Int. Ed. Engl. 1986, 25, 253.
16. J. Schwartz, J. Labinger, Angew. Chem. 1976, 88, 402; Angew. Chem. Int. Ed Engl. 1976, 15, 333.
17. J. Schwartz, J. Labinger, Angew. Chem. 1976, 88, 402; Angew. Chem. Int. Ed Engl. 1976, 15, 333.
18. G. Erker, K. Kropp, C. Krüger, A.-P. Chiang, Chem. Ber. 1982, 115, 2447.
19. int = 0.100) were used. The structure was solved using the program SHELXS-97 and refined (326 parameter) using the program SHELXL-97 to R1 = 0.0525, wR2 = 0.1137 (all data) (1 > 2σ(I); both programs from G. M. Sheldrick, Universität Göttingen. 1997). The positions of the Zr-H hydrogen atoms were localized in the difference fourier map and refined; non-hydrogen atoms were anisotropically refined. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Centre as supplementary publication no. CCDC-116996. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB 1EZ, UK (fax: (+ 44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
20. Z. Hou, T. L. Breen, D. W. Stephan, Organometallics 1993, 12, 3158, and references therein.
21. J. B. Jones, J. Petersen, Inorg. Chem. 1981, 20, 2889.
22. M. F. Hawthorne, Z. Zheng, Acc. Chem. Res. 1997, 30, 267.
23. The density functional calculations have been carried out using the program described in: C. van Wüllen, Chem. Phys. Lett. 1994, 219, 8, and references therein. Triple zeta-type basis sets were taken for the light atoms H to Cl, and quasirelativistic, effective core potentials were used for the Zr atoms, together with an 8s7p6d valence basis contracted to 6s5p4d.
24. W. Kutzelnigg, Angew. Chem. 1984, 96, 262: Angew. Chem. Int. Ed. Engl. 1984, 23, 272.
25. W. Kutzelnigg, Angew. Chem. 1984, 96, 262: Angew. Chem. Int. Ed. Engl. 1984, 23, 272.