Novel organophosphorus cage compound produced by an unexpected oxidative coupling of 1,2,4-triphosphole: Crystal and molecular structures of two isomers of formula P6C4But4CHSiMe3

Journal of the Brazilian Chemical Society

Volumn 13, Issue 5, 2002, Pages 555-558

  Araujo, Maria Helena ^a   Rajão, Daniel A ^a   Doriguetto, Antonio C ^b   Ellena, Javier ^b   Castellano, Eduardo E ^b   Hitchcock, Peter B ^c   Caliman, Vinicius ^a  

^a FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

Multinuclear NMR; Organophosphorus compounds; X ray molecular structure

Indexed keywords

1,2,3 TRIPHOSPHOLE; ORGANOPHOSPHORUS COMPOUND; PHOSPHORUS DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ISOMER; OXIDATION; SPECTROSCOPY; SYNTHESIS; X RAY DIFFRACTION;

EID: 0036458975     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50532002000500002     Document Type: Article

References (23)

1. Dillon, K. B.; Matthey, F.; Nixon, J. F.; Phosphorus: The Carbon Copy, John Wiley: Chichester, 1998, p. 266 and references therein.
2. Becker, G.; Gresser, G.; Uhl, W.; Z. Naturforsch., B 1981, 36, 16.
3. Streubel, R.; Angew. Chem., Int. Ed. Engl. 1995, 34, 436; Caliman, V.; Hitchcock, P. B.; Nixon, J. F.; Hofmann, M.; Schleyer, P. R.; Angew. Chem., Int. Ed. Engl. 1994, 33, 2202; Geissler, B.; Wettling, T.; Barth, S.; Binger, P.; Regitz, M.; Synthesis 1994, 1337; Tabellion, F.; Nachbauer, A.; Leininger, S.; Peters, C.; Preuss, F.; Regitz, M.; Angew. Chem., Int. Ed. Engl. 1998, 37, 1233.
4. Streubel, R.; Angew. Chem., Int. Ed. Engl. 1995, 34, 436; Caliman, V.; Hitchcock, P. B.; Nixon, J. F.; Hofmann, M.; Schleyer, P. R.; Angew. Chem., Int. Ed. Engl. 1994, 33, 2202; Geissler, B.; Wettling, T.; Barth, S.; Binger, P.; Regitz, M.; Synthesis 1994, 1337; Tabellion, F.; Nachbauer, A.; Leininger, S.; Peters, C.; Preuss, F.; Regitz, M.; Angew. Chem., Int. Ed. Engl. 1998, 37, 1233.
5. Streubel, R.; Angew. Chem., Int. Ed. Engl. 1995, 34, 436; Caliman, V.; Hitchcock, P. B.; Nixon, J. F.; Hofmann, M.; Schleyer, P. R.; Angew. Chem., Int. Ed. Engl. 1994, 33, 2202; Geissler, B.; Wettling, T.; Barth, S.; Binger, P.; Regitz, M.; Synthesis 1994, 1337; Tabellion, F.; Nachbauer, A.; Leininger, S.; Peters, C.; Preuss, F.; Regitz, M.; Angew. Chem., Int. Ed. Engl. 1998, 37, 1233.
6. Streubel, R.; Angew. Chem., Int. Ed. Engl. 1995, 34, 436; Caliman, V.; Hitchcock, P. B.; Nixon, J. F.; Hofmann, M.; Schleyer, P. R.; Angew. Chem., Int. Ed. Engl. 1994, 33, 2202; Geissler, B.; Wettling, T.; Barth, S.; Binger, P.; Regitz, M.; Synthesis 1994, 1337; Tabellion, F.; Nachbauer, A.; Leininger, S.; Peters, C.; Preuss, F.; Regitz, M.; Angew. Chem., Int. Ed. Engl. 1998, 37, 1233.
7. Caliman, V.; Quim. Nova 2000, 23, 346.
8. Hu, D.; Schäufele, H.; Pritzkow, H.; Zenneck. U.; Angew. Chem., Int. Ed. Engl. 1989, 28, 900.
9. Avent, A. G.; Cloke, F. G. N.; Francis, M. D.; Hitchcock, P. B.; Nixon, J. F.; Chem. Commun. 2000, 879.
10. Lappert, M. F.; Liu, D. S.; J. Organomet. Chem. 1995, 500, 203.
11. 2) (2.31 mmol) in 15 mL of DME, at -30°C and the resulting mixture was stirred for 20 h. The LiBr formed during the reaction was filtered off and the solvent evaporated under vacuum. The residue was purified by column chromatography (kieselgel/hexane) to give two yellow bands. The first was characterised as compound 1 (250 mg, 20%), and the second as compound 2 (200 mg, 16%). Recrystalisation from hexane at room temperature afforded yellow crystals suitable for X-ray diffraction study for both compounds.
12. Caliman, V.; Hitchcock, P. B.; Nixon, J. F.; Heteroatom Chem. 1998, 9, 1.
13. Hitchcock, P. B.; Nixon, J. F.; Buyukkidan, N. S.; Chem. Commun. 2001, 2720.
14. +.
15. 2) = 0.123 for all data.
16. Maigrot, N.; Ricard, L.; Charrier, C.; Golf, P. L.; Mathey, F.; Bull. Soc. Chim. Fr. 1992, 129, 76; Bevierre, M. O.; Mercier, F.; Ricard, L.; Mathey, F.; Bull. Soc. Chim. Fr. 1992, 129, 1; Bartsch, R.; Hitchcock, P. B.; Nixon, J. F.; J. Chem. Soc., Chem. Commun. 1989, 1046.
17. Maigrot, N.; Ricard, L.; Charrier, C.; Golf, P. L.; Mathey, F.; Bull. Soc. Chim. Fr. 1992, 129, 76; Bevierre, M. O.; Mercier, F.; Ricard, L.; Mathey, F.; Bull. Soc. Chim. Fr. 1992, 129, 1; Bartsch, R.; Hitchcock, P. B.; Nixon, J. F.; J. Chem. Soc., Chem. Commun. 1989, 1046.
18. Maigrot, N.; Ricard, L.; Charrier, C.; Golf, P. L.; Mathey, F.; Bull. Soc. Chim. Fr. 1992, 129, 76; Bevierre, M. O.; Mercier, F.; Ricard, L.; Mathey, F.; Bull. Soc. Chim. Fr. 1992, 129, 1; Bartsch, R.; Hitchcock, P. B.; Nixon, J. F.; J. Chem. Soc., Chem. Commun. 1989, 1046.
19. Geissler, B.; Barth, S.; Bergsträsser, U.; Slany, M.; Durkin, J.; Hitchcock, P. B.; Hofmann, M.; Binger, P.; Nixon, J. F.; Schleyer, P. R.; Regitz. M.; Angew. Chem., Int. Ed. Engl. 1995, 34, 484; Gudat, D.; Niecke, E.; Arif, A. M.; Cowley, A. H.; Quashie, S.; Organometallics 1986, 5, 593; Kroto, H. W.; Nixon, J. F.; Ohashi, O.; Ohno, K.; Simmons, N. P.; J. Mol. Spectrosc. 1984, 103, 113.
20. Geissler, B.; Barth, S.; Bergsträsser, U.; Slany, M.; Durkin, J.; Hitchcock, P. B.; Hofmann, M.; Binger, P.; Nixon, J. F.; Schleyer, P. R.; Regitz. M.; Angew. Chem., Int. Ed. Engl. 1995, 34, 484; Gudat, D.; Niecke, E.; Arif, A. M.; Cowley, A. H.; Quashie, S.; Organometallics 1986, 5, 593; Kroto, H. W.; Nixon, J. F.; Ohashi, O.; Ohno, K.; Simmons, N. P.; J. Mol. Spectrosc. 1984, 103, 113.
21. Geissler, B.; Barth, S.; Bergsträsser, U.; Slany, M.; Durkin, J.; Hitchcock, P. B.; Hofmann, M.; Binger, P.; Nixon, J. F.; Schleyer, P. R.; Regitz. M.; Angew. Chem., Int. Ed. Engl. 1995, 34, 484; Gudat, D.; Niecke, E.; Arif, A. M.; Cowley, A. H.; Quashie, S.; Organometallics 1986, 5, 593; Kroto, H. W.; Nixon, J. F.; Ohashi, O.; Ohno, K.; Simmons, N. P.; J. Mol. Spectrosc. 1984, 103, 113.
22. +.
23. 2) = 0.1662 for all data.