Synthesis and Resolution of the Configurationally Stable Tris(tetra-chlorobenzenediolato)phosphate(v) Ion

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 6, 1997, Pages 608-610

  Lacour, Jérôme ^a   Ginglinger, Catherine ^a   Grivet, Chantal ^a   Bernardinelli, Gérald ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Chirality; Cinchonidine; Enantiomeric resolution; Phosphorus

Indexed keywords

EID: 0030893503     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199706081     Document Type: Article

References (43)

1. For compounds with hexacoordinated phosphorus, see a) M. J. Gallagher, I. D. Jenkins, Top. in Stereochem. 1968, 3, 76; b) D. Hellwinkel in Organic Phosphorus Compounds, Vol. 3 (Eds.: G. M. Kosolapoff, L. Maier), Wiley, New York, 1972, p. 185; c) R. Luckenbach in Methoden der Organischen Chemie, Band E2 (Ed.: M. Regitz), Thieme, Stuttgart 1982, p. 897; d) R. A. Cherkasov, N. A. Polezhaeva Usp. Khim. 1987, 56, 287; Russ. Chem. Rev. 1987, 56, 163; e) R. Burgada, R. Setton in The Chemistry of Organophosphorus Compounds, Vol. 3 (Ed.: F. R. Hartley), Wiley, New York 1994, p. 185; f) R. R. Holmes, Chem. Rev. 1996, 96, 927.
2. For compounds with hexacoordinated phosphorus, see a) M. J. Gallagher, I. D. Jenkins, Top. in Stereochem. 1968, 3, 76; b) D. Hellwinkel in Organic Phosphorus Compounds, Vol. 3 (Eds.: G. M. Kosolapoff, L. Maier), Wiley, New York, 1972, p. 185; c) R. Luckenbach in Methoden der Organischen Chemie, Band E2 (Ed.: M. Regitz), Thieme, Stuttgart 1982, p. 897; d) R. A. Cherkasov, N. A. Polezhaeva Usp. Khim. 1987, 56, 287; Russ. Chem. Rev. 1987, 56, 163; e) R. Burgada, R. Setton in The Chemistry of Organophosphorus Compounds, Vol. 3 (Ed.: F. R. Hartley), Wiley, New York 1994, p. 185; f) R. R. Holmes, Chem. Rev. 1996, 96, 927.
3. For compounds with hexacoordinated phosphorus, see a) M. J. Gallagher, I. D. Jenkins, Top. in Stereochem. 1968, 3, 76; b) D. Hellwinkel in Organic Phosphorus Compounds, Vol. 3 (Eds.: G. M. Kosolapoff, L. Maier), Wiley, New York, 1972, p. 185; c) R. Luckenbach in Methoden der Organischen Chemie, Band E2 (Ed.: M. Regitz), Thieme, Stuttgart 1982, p. 897; d) R. A. Cherkasov, N. A. Polezhaeva Usp. Khim. 1987, 56, 287; Russ. Chem. Rev. 1987, 56, 163; e) R. Burgada, R. Setton in The Chemistry of Organophosphorus Compounds, Vol. 3 (Ed.: F. R. Hartley), Wiley, New York 1994, p. 185; f) R. R. Holmes, Chem. Rev. 1996, 96, 927.
4. For compounds with hexacoordinated phosphorus, see a) M. J. Gallagher, I. D. Jenkins, Top. in Stereochem. 1968, 3, 76; b) D. Hellwinkel in Organic Phosphorus Compounds, Vol. 3 (Eds.: G. M. Kosolapoff, L. Maier), Wiley, New York, 1972, p. 185; c) R. Luckenbach in Methoden der Organischen Chemie, Band E2 (Ed.: M. Regitz), Thieme, Stuttgart 1982, p. 897; d) R. A. Cherkasov, N. A. Polezhaeva Usp. Khim. 1987, 56, 287; Russ. Chem. Rev. 1987, 56, 163; e) R. Burgada, R. Setton in The Chemistry of Organophosphorus Compounds, Vol. 3 (Ed.: F. R. Hartley), Wiley, New York 1994, p. 185; f) R. R. Holmes, Chem. Rev. 1996, 96, 927.
5. For compounds with hexacoordinated phosphorus, see a) M. J. Gallagher, I. D. Jenkins, Top. in Stereochem. 1968, 3, 76; b) D. Hellwinkel in Organic Phosphorus Compounds, Vol. 3 (Eds.: G. M. Kosolapoff, L. Maier), Wiley, New York, 1972, p. 185; c) R. Luckenbach in Methoden der Organischen Chemie, Band E2 (Ed.: M. Regitz), Thieme, Stuttgart 1982, p. 897; d) R. A. Cherkasov, N. A. Polezhaeva Usp. Khim. 1987, 56, 287; Russ. Chem. Rev. 1987, 56, 163; e) R. Burgada, R. Setton in The Chemistry of Organophosphorus Compounds, Vol. 3 (Ed.: F. R. Hartley), Wiley, New York 1994, p. 185; f) R. R. Holmes, Chem. Rev. 1996, 96, 927.
6. For compounds with hexacoordinated phosphorus, see a) M. J. Gallagher, I. D. Jenkins, Top. in Stereochem. 1968, 3, 76; b) D. Hellwinkel in Organic Phosphorus Compounds, Vol. 3 (Eds.: G. M. Kosolapoff, L. Maier), Wiley, New York, 1972, p. 185; c) R. Luckenbach in Methoden der Organischen Chemie, Band E2 (Ed.: M. Regitz), Thieme, Stuttgart 1982, p. 897; d) R. A. Cherkasov, N. A. Polezhaeva Usp. Khim. 1987, 56, 287; Russ. Chem. Rev. 1987, 56, 163; e) R. Burgada, R. Setton in The Chemistry of Organophosphorus Compounds, Vol. 3 (Ed.: F. R. Hartley), Wiley, New York 1994, p. 185; f) R. R. Holmes, Chem. Rev. 1996, 96, 927.
7. For compounds with hexacoordinated phosphorus, see a) M. J. Gallagher, I. D. Jenkins, Top. in Stereochem. 1968, 3, 76; b) D. Hellwinkel in Organic Phosphorus Compounds, Vol. 3 (Eds.: G. M. Kosolapoff, L. Maier), Wiley, New York, 1972, p. 185; c) R. Luckenbach in Methoden der Organischen Chemie, Band E2 (Ed.: M. Regitz), Thieme, Stuttgart 1982, p. 897; d) R. A. Cherkasov, N. A. Polezhaeva Usp. Khim. 1987, 56, 287; Russ. Chem. Rev. 1987, 56, 163; e) R. Burgada, R. Setton in The Chemistry of Organophosphorus Compounds, Vol. 3 (Ed.: F. R. Hartley), Wiley, New York 1994, p. 185; f) R. R. Holmes, Chem. Rev. 1996, 96, 927.
8. a) D. Hellwinkel, Angew. Chem. 1965, 77, 378; Angew. Chem. Int. Ed. Engl. 1965, 4, 356;
9. a) D. Hellwinkel, Angew. Chem. 1965, 77, 378; Angew. Chem. Int. Ed. Engl. 1965, 4, 356;
10. b) Chem. Ber. 1966, 99, 3628;
11. c) ibid. 1966, 99, 3660;
12. d) ibid. 1966, 99, 3642;
13. e) D. Hellwinkel, S. F. Mason, J. Chem. Soc. B 1970, 640;
14. f) D. Hellwinkel, H. J. Wilfinger, Chem. Ber. 1970, 103, 1056;
15. g) A. Munoz, G. Gence, M. Koenig, R. Wolf. Bull. Soc. Chim. Fr. 1975, 1433;
16. h) M. Koenig, A. Klaebe, A. Munoz, R. Wolf, J. Chem. Soc. Perkin Trans. 2 1976, 955;
17. i) A. Klaebe, M. Koenig, R. Wolf, P. Ahlberg, J. Chem. Soc. Dalton Trans. 1977, 570;
18. j) J. Cavezzan, G. Etemad-Moghadam, M. Koenig, A. Klaebe, Tetrahedron Lett. 1979, 795;
19. k) M. Koenig, A. Klaebe, A. Munoz, R. Wolf, J. Chem. Soc. Perkin Trans. 2 1979, 40;
20. l) D. Hellwinkel Ger. Patent 1 235 913, 1967; Chem. Abstr. 1967, 67, 64537.
21. l) D. Hellwinkel Ger. Patent 1 235 913, 1967; Chem. Abstr. 1967, 67, 64537.
22. The absolute configuration of 1 (P or M) is unknown.
23. X-ray structure analyses of alkylammonium salts of 1 show hydrogen bonds between the hydrogen atoms of the ammonium cation and the oxygen atoms of the phosphate group: a) H. R. Allcock, E. C. Bissell, J. Am. Chem. Soc. 1973, 95, 3154; b) H. R. Allcock, E. C. Bissell, J. Chem. Soc. Chem. Commun. 1972, 676.
24. X-ray structure analyses of alkylammonium salts of 1 show hydrogen bonds between the hydrogen atoms of the ammonium cation and the oxygen atoms of the phosphate group: a) H. R. Allcock, E. C. Bissell, J. Am. Chem. Soc. 1973, 95, 3154; b) H. R. Allcock, E. C. Bissell, J. Chem. Soc. Chem. Commun. 1972, 676.
25. There has been no direct observation of the phosphorane intermediate 2. The geometry of 2 could be trigonal bipyramidal, square pyramidal, or any structure in between. If 2 were square pyramidal, it would be achiral, and ring opening of 1 would be a direct racemization. For the geometry of spirophosphoranes, see a) T. E. Clark, R. O. Day, R. R. Holmes, Inorg. Chem. 1979, 18, 1653; b) ibid. 1979, 18, 1660; c) ibid. 1979, 18, 1668; d) A. Schmidpeter, T. von Criegern, W. S. Sheldrick, D. Schomburg, Tetrahedron Lett. 1978, 2857.
26. There has been no direct observation of the phosphorane intermediate 2. The geometry of 2 could be trigonal bipyramidal, square pyramidal, or any structure in between. If 2 were square pyramidal, it would be achiral, and ring opening of 1 would be a direct racemization. For the geometry of spirophosphoranes, see a) T. E. Clark, R. O. Day, R. R. Holmes, Inorg. Chem. 1979, 18, 1653; b) ibid. 1979, 18, 1660; c) ibid. 1979, 18, 1668; d) A. Schmidpeter, T. von Criegern, W. S. Sheldrick, D. Schomburg, Tetrahedron Lett. 1978, 2857.
27. There has been no direct observation of the phosphorane intermediate 2. The geometry of 2 could be trigonal bipyramidal, square pyramidal, or any structure in between. If 2 were square pyramidal, it would be achiral, and ring opening of 1 would be a direct racemization. For the geometry of spirophosphoranes, see a) T. E. Clark, R. O. Day, R. R. Holmes, Inorg. Chem. 1979, 18, 1653; b) ibid. 1979, 18, 1660; c) ibid. 1979, 18, 1668; d) A. Schmidpeter, T. von Criegern, W. S. Sheldrick, D. Schomburg, Tetrahedron Lett. 1978, 2857.
28. There has been no direct observation of the phosphorane intermediate 2. The geometry of 2 could be trigonal bipyramidal, square pyramidal, or any structure in between. If 2 were square pyramidal, it would be achiral, and ring opening of 1 would be a direct racemization. For the geometry of spirophosphoranes, see a) T. E. Clark, R. O. Day, R. R. Holmes, Inorg. Chem. 1979, 18, 1653; b) ibid. 1979, 18, 1660; c) ibid. 1979, 18, 1668; d) A. Schmidpeter, T. von Criegern, W. S. Sheldrick, D. Schomburg, Tetrahedron Lett. 1978, 2857.
29. 1 =10.87. For a list of pKa values, see D. H. Rosenblatt, J. Epstein, M. Levitch, J. Am. Chem. Soc. 1953, 75, 3277.
30. 3: I. V. Shevchenko, A. Fischer, P. G. Jones, R. Schmutzler, Chem. Ber. 1992, 125, 1325.
31. Yields of isolated products.
32. 31P-NMR-Spektroskopie, Thieme, Stuttgart, 1993, p. 62.
33. Cinchonidine has been used successfully for the resolution of tris(benzenediolato)arsenate: a) J. H. Craddock, M. M. Jones, J. Am. Chem. Soc. 1961, 83, 2839; b) J. Mason, S. F. Mason, Tetrahedron 1967, 23, 1919; c) G. E. Ryschkewitsch, J. M. Garett, J. Am. Chem. Soc. 1968, 90, 7234.
34. Cinchonidine has been used successfully for the resolution of tris(benzenediolato)arsenate: a) J. H. Craddock, M. M. Jones, J. Am. Chem. Soc. 1961, 83, 2839; b) J. Mason, S. F. Mason, Tetrahedron 1967, 23, 1919; c) G. E. Ryschkewitsch, J. M. Garett, J. Am. Chem. Soc. 1968, 90, 7234.
35. Cinchonidine has been used successfully for the resolution of tris(benzenediolato)arsenate: a) J. H. Craddock, M. M. Jones, J. Am. Chem. Soc. 1961, 83, 2839; b) J. Mason, S. F. Mason, Tetrahedron 1967, 23, 1919; c) G. E. Ryschkewitsch, J. M. Garett, J. Am. Chem. Soc. 1968, 90, 7234.
36. D = -78.8, c = 0.08 in EtOH.
37. 2). 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-179-150. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: Int. code +(1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk).
38. E. Blanc, D. Schwarzenbach, H. D. Flack, J. Appl. Crystallogr. 1991, 24, 1035.
39. P. Main, S. J. Fiske, S. E. Hull, E. Lessinger, G. Germain, J.-P. Declercq, M. M. Woolfson, A System of Computer Programs for the Automatic Solution of Crystal Structures from X-Ray Diffraction Data, Universities of York (UK) and Louvain-la-Neuve (Belgium), 1987.
40. S. R. Hall, H. D. Flack, J. M. Stewart, Eds. XTAL3.2 User's Manual, Universities of Western Australia and Maryland (USA), 1972.
41. C. K. Johnson, ORTEP II; Report ORNL-5138, Oak ridge National Laboratory, Oak Ridge TN, 1976.
42. G. Bernardinelli, H. D. Flack, Acta Cryst. Sect A. 1985, 41, 500.
43. P-O mean bond lengths in previously reported 6 and 1 are 1.714 (ref. [7]) and 1.717 Å(ref. [4]), respectively.