The first flights of a molecular shuttle transporting elements: Easy one-pot formation of organic cyclic arsanes, stibanes and bismutanes

Chemistry - A European Journal

Volumn 15, Issue 3, 2009, Pages 597-599

  Baccolini, Graziano ^a   Boga, Carla ^a   Mazzacurati, Marzia ^a   Micheletti, Gabriele ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Antimony; Arsenic; Bismuth; Phosphorus heterocycles; Pnictides

Indexed keywords

ANTIMONY; ARSENIC; BISMUTH; PHOSPHORUS;

IN-SITU; PHOSPHORUS HETEROCYCLES; PNICTIDES; REACTION MIXTURES; TRANSPORT PROCESSES;

NONMETALS;

EID: 58449106210     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802007     Document Type: Article

References (42)

1. a) W. Levason, G. Reid, Coord. Chem. Rev. 2006, 250, 2565-2594, and references therein;
2. b) H. Werner. Angew. Chem. 2004, 116, 956-972;
3. Angew. Chem. Int. Ed. 2004, 43, 938-954;
4. c) N. A. Compton, R. J. Erringlon, C. Nicholas, Adv. Organomet. Chem. 1990, 31, 91-182;
5. d) C. A. McAuliffe, W. Levason, Phosphlne, Arsine and Stibine Complexes of the Transition Elements, Elsevier, Amsterdam, 1978;
6. e) J. L. Wardell, Arsenic Antimony, and Bismuth in Comprehensive Organometallic Chemistry II, Vol.2 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson, A. G. Davies), Pergamon, Oxford, 1995.
7. a) G. G. Briand, N. Burford, Chem. Rev. 1999, 99, 2601-2657;
8. b) W. R. Cullen, K. J. Reimer. Chem. Rev. 1989, 89, 713-764;
9. Y.-Z. Huang, Acc. Chem. Res. 1992, 25, 182-187;
10. c) Inorganic Materials (Eds.: D. W. Bruce, D. O. Hare), Wiley, New York, 1992;
11. d) Chemical Vapor Deposition: Principles and Applications (Eds.: M.-L. Hitchman, K.-F. Jensen), Academic, London, 1993.
12. a) J. Mishra, A. Saxena, S. Sing. Curr. Med. Chem. 2007, 14, 1153-1169;
13. b) E. Guillamet, A. Creus, J. Ponti, E. Sabbioni, S. Fortaner, R. Marcos, Mutagenesis 2004, 19, 129-135;
14. c) T. Kotani, D. Nagai, K. Asahi, H. Suzuki, F. Yamao, N. Kataoka, T. Yagura. Antimicrob. Agents Chemother. 2005, 49, 2729-2734;
15. d) I. Mancini, G. Guella, M. Frostin, E. Hnawia, D. Laurent, C. Debitus, F. Pietra. Chem. Eur. J. 2006, 12, 8989-8994.
16. a) M. D. Smith, Product Class I: Arsenic Compounds, Science of Synthesis Vol.4 (Ed.: 1. Fleming), Thieme, Stuttgart, 2002, pp. 13-51;
17. b) J. W. Burton, Product Class 2: Antimony Compounds, Science of Synthesis Vol. 4 (Ed.: I. Fleming), Thieme. Stuttgart, pp. 53-57;
18. c) H Suzuki, T. Ikegami, Product Class 3: Bismuth Compounds, Science of Synthesis Vol. 4 (Ed.: I. Fleming), Thieme, Stuttgart, pp. 77-116.
19. a) G. Baccolini, C. Boga, U. Negri, Synlett 2000, 1685-1687;
20. b) G. Baccolini, C. Boga, R. A. Buscaroli, Eur. J. Org. Chem. 2001, 3421-3424;
21. c) G. Baccolini; C. Boga, M. Galeotti, Angew. Chem. 2004, 116, 3120-3122;
22. Angew. Chem. Int. Ed. 2004, 43, 3058-3060.
23. a) G. Baccolini, E. Mezzina, P. E. Todesco, E. Foresti, J. Chem. Soc. Chem. Commun., 1988, 304-305;
24. b) G. Baccolini, M. Beghelli, C. Boga, Heteroatom. Chem. 1997, 8, 551-556.
25. G. Baccolini, C. Boga, M. Mazzacurati, J. Org. Chem. 2005, 70, 4114-4171.
26. a) G. Baccolini, C. Boga, M. Mazzacurati, Eur. J. Org. Chem. 2007, 4529-4534.
27. a) F. G. Mann, The Heterocyclic Derivatives of Phosphorus, Arsenic, Antimony and Bismuth, Wiley-Interscience: New York, 1970;
28. b) R. E. Atkinson, Heterocyclic Rings containing Arsenic, Antimomy or Bismuth, Comprehensive Heterocyclic Chemistry, Vol. 1 (Eds.: A. R. Katritzky, C. W. Rees), Pergamon, Oxford, 1984, pp. 539-561;
29. c) K. C. Caster, Arsoles, Stiboles, and Bismoles, Comprehensive Heterocyclic Chemistry II. Vol. 2 (Eds.: A. R. Katritzky, C. W. Rees, E. F. Scriven, C. W. Bird), Pergamon, Oxford, 1996, pp. 891-895.
30. 3, see the Supporting Information.
31. a) C. Jones, Coord. Chem. Rev. 2001, 215, 151-169;
32. b) J. W. Wielandt, N. L. Kilah, A. C. Willis, S. B. Wild, Chem. Commun. 2006, 3679-3680.
33. a) R. Luckenbach, Dynamic Stereochemistry of Pentacoordinated Phosphorus and Related Elements, Thieme, Stuttgart, 1973;
34. b) G. Wittig, D. Hellwinkel, Angew. Chem. 1962, 74, 76;
35. Angew. Chem. Int. Ed. Engl. 1962, 1, 53;
36. c) D. Hellwinkel, M. Bach, Justus Liehigs Ann. Chem. 1968, 720, 198.
37. a) Chemistry of Hypervalent Compounds (Ed.: K. Akiba), Wiley-VCH. Weinheim, 1999;
38. b) Organobismuth Chemistry (Eds.: H. Suzuki, Y. Malano), Elsevier, Amsterdam, 2001.
39. G. Baccolini, C. Boga, M. Mazzacurati, Tetrahedron 2007, 63, 12595-12600.
40. For reviews on hypervalent phosphorus see: a) R. R. Holmes, Pentacoordinated Phosphorus Structure and Spectroscopy, ACS Monograph 175, Vol. 1-2, American Chemical Society, Washington, 1980;
41. b) R. R. Holmes, Acc. Chem. Res. 1998, 31, 535-542;
42. c) C. Y. Wong, D. K. Kennepohl, R. G. Cavell, Chem. Rev. 1996, 96, 1917-1951.