Efficient one-pot synthesis of secondary cyclic phosphanes with easy regeneration of the phosphorus-donor reagent used

Angewandte Chemie - International Edition

Volumn 43, Issue 23, 2004, Pages 3058-3060

  Baccolini, Graziano ^a   Boga, Carla ^a   Galeotti, Matteo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Hypervalent compounds; Phosphanes; Phosphorus heterocycles; Synthetic methods

Indexed keywords

PHOSPHORUS; PURIFICATION; SOLUTIONS; THERMAL EFFECTS;

CHEMICAL REAGENTS; CHEMICAL TREATMENTS; ROOM TEMPERATURE;

SYNTHESIS (CHEMICAL);

ALKANE DERIVATIVE; PHOSPHORUS; PHOSPHORUS DERIVATIVE;

ARTICLE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; ROOM TEMPERATURE; SYNTHESIS;

EID: 4544240698     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200453820     Document Type: Article

References (27)

1. a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
2. b) M. J. Burk, M. F. Gross, J. P. Martinez, J. Am. Chem. Soc. 1995, 117, 9375-9376;
3. c) M. J. Burk, A. Pizzano, J. A. Martin, L. M. Liable-Sands, A. L. Rheingold, Organometallics 2000, 19, 250-260;
4. d) Q. Jiang, D. Xiao, Z. Zhang, P. Cao, X. Zang, Angew. Chem. 1999, 111, 578-580; Angew. Chem. Int. Ed. 1999, 38, 516-518.
5. d) Q. Jiang, D. Xiao, Z. Zhang, P. Cao, X. Zang, Angew. Chem. 1999, 111, 578-580; Angew. Chem. Int. Ed. 1999, 38, 516-518.
6. a) K. Dimroth, Heterocyclic Rings Containing Phosphorus in Comprehensive Heterocyclic Chemistry, Vol. 1 (Eds.: A. R. Katritzky, C. W. Rees), Pergamon, New York, 1984, pp. 500, 513;
7. b) D. Quin, Phospholes in Comprehensive Heterocyclic Chemistry II, Vol. 2 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven, C. W. Bird), Pergamon, New York, 1996, pp. 826-831;
8. c) D. G. Hewitt, Six-membered Rings with One Phosphorus Atom in Comprehensive Heterocyclic Chemistry II, Vol. 5 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven, A. McKillop), Pergamon, New York, 1996, p. 639-668.
9. A. B. Burg, P. J. Slota, J. Am. Chem. Soc. 1960, 82, 2148-2151.
10. R. A. Aitken, W. Masamba, N. J. Wilson, Tetrahedron Lett. 1997, 35, 8417-8420.
11. J. B. Lambert, W. L. Oliver, Tetrahedron 1971, 27, 4245-4254.
12. a) D. M. Schubert, A. D. Norman, Inorg. Chem. 1984, 23, 4130-4131;
13. b) D. M. Schubert, P. F. Brandt, A. D. Norman, Inorg. Chem. 1996, 35, 6204-6209;
14. c) P. F. Brandt, D. M. Schubert, A. D. Norman, Inorg. Chem. 1997, 36, 1728-1731.
15. M. R. Douglass, T. J. Marks, J. Am. Chem. Soc. 2000, 122, 1824-1825.
16. a) G. Baccolini, E. Mezzina, P. E. Todesco, E. Foresti, J. Chem. Soc. Chem. Commun. 1988, 304-305;
17. b) G. Baccolini, M. Beghelli, C. Boga, Heteroat. Chem. 1997, 8, 551-556;
18. c) R. Gang Wu, E. Wasylishen, W. P. Power, G. Baccolini, Can. J. Chem. 1992, 70, 1229-1235.
19. G. Baccolini, G. Orsolan, E. Mezzina, Tetrahedron Lett. 1995, 36, 447-450.
20. G. Baccolini, C. Boga, U. Negri, Synlett 2000, 1685-1687.
21. For reviews on pentacoordinate and hexacoordinate phosphorus, see a) R. R. Holmes, Pentacordinate Phosphorus Structure and Spectroscopy, Vols. I and II, ACS Monograph 175, American Chemical Society, Washington, DC, 1980;
22. b) C. Y. Wong, D. K. Kennepohl, R. G. Cavell, Chem. Rev. 1996, 96, 1917-1951;
23. c) R. R. Holmes, Acc. Chem. Res. 1998, 31, 535-542.
24. 2: 278.0353, found: 278.0355.
25. a) B. M. Trost, Angew. Chem. 1995, 107, 285-307; Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281;
26. a) B. M. Trost, Angew. Chem. 1995, 107, 285-307; Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281;
27. b) B. M. Trost, Acc. Chem. Res. 2002, 35, 695-705.