Synthesis, structure, and reactivity of a stabilized phosphiranylium salt

Angewandte Chemie - International Edition

Volumn 49, Issue 32, 2010, Pages 5485-5488

  Jansen, Helen ^a   Läng, Florian B ^b   Slootweg, J C ^a   Ehlers, Andreas W ^a   Lutz, Martin ^c   Lammertsma, Koop ^a   Grützmacher, Hansjörg ^b  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

^b ETH ZURICH   (Switzerland)

^c UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Carbenes; Cations; Heterocycles; Phosphiranes; Phosphorus

Indexed keywords

CARBENES; HETEROCYCLES; METHYL TRIFLATES; N-HETEROCYCLIC CARBENES; NUCLEOPHILIC ADDITIONS; PHOSPHIRANES;

ADDITION REACTIONS; CARBON INORGANIC COMPOUNDS; PHOSPHORUS; POSITIVE IONS;

ORGANIC COMPOUNDS;

CARBENE; CATION; DRUG DERIVATIVE; INORGANIC SALT; MESYLIC ACID DERIVATIVE; METHANE; PHOSPHORUS DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID METHYL ESTER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CATIONS; MESYLATES; METHANE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHORUS COMPOUNDS; SALTS;

EID: 77955036990     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201000901     Document Type: Article

References (62)

1. a) F. Mathey, Pure Appl. Chem. 1987, 59, 993-998;
2. b) F. Mathey, Chem. Rev. 1990, 90, 997-1025;
3. c) F. Mathey, M. Regitz in Comprehensive Heterocyclic Chemistry II, Vol. 1A (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Amsterdam, 1997, pp. 277-304;
4. d) F. Mathey, M. Regitz in PhosphorusCarbon Heterocyclic Chemistry: The Rise of a New Domain (Ed.: F. Mathey), Pergamon, Amsterdam, 2001, pp. 17-55.
5. a) K. Lammertsma, Top. Curr. Chem. 2003, 229, 95-119;
6. b) K. Lammertsma, M. J. M. Vlaar, Eur. J. Org. Chem. 2002, 1127-1138;
7. c) F. Mathey, N. H. Tran Huy, A. Marinetti, Helv. Chim. Acta 2001, 84, 2938-2957;
8. d) X. Li, S. I. Weismann, T.-S. Lin, P. P. Gasper, A. H. Cowley, A. I. Smirnov, J. Am. Chem. Soc. 1994, 116, 7899-7900;
9. e) G. Bucher, M. L. G. Borst, A.W. Ehlers, K. Lammertsma, S. Ceola, M. Huber, D. Grote, W. Sander, Angew. Chem. 2005, 111, 3353-3357;
10. Angew. Chem. Int. Ed. 2005, 44, 3289-3293.
11. S. Kobayashi, J.-I. Kadokawa, Macromol. Rapid Commun. 1994, 15, 567-571.
12. a) J. Liedtke, H. Rüegger, S. Loss, H. Grützmacher, Angew. Chem. 2000, 112, 2596-2599;
13. Angew. Chem. Int. Ed. 2000, 39, 2478-2481;
14. b) C. Laporte, G. Frison, H. Grützmacher, A.C. Hillier, W. Sommer, S. P. Nolan, Organometallics 2003, 22, 2202-2208, and references therein.
15. a) R. Chen, Y.-H. Cheng, L. Liu, X.-S. Li, Q.-X. Guo, Res Chem. Interned. 2002, 25, 41-48;
16. b) X. Liu, D. M. Ivanova, D. Giblin, M. L. Gross, P. P. Gaspar, Organometallics 2005, 24, 3125-3135;
17. c) W. W. Schoeller, U. Tubbesing, J. Mol. Struct. 1995, 343, 4955;
18. d) A. Largo, C. Barrientos, X. Lopez, F. P. Cossio, J. M. Ugalde, J. Phys. Chem. 1995, 99, 6432-6440;
19. e) W. W. Schoeller, Top. Curr. Chem. 2003, 229, 75-94.
20. a) A in solution at low temperature: K. K. Laali, B. Geissler, O. Wagner, J. Hoffmann, R. Armbrust, W. Eisfeld, M. Regitz, J. Am. Chem. Soc. 1994, 116, 9407-9408. For stable transitionmetal complexes of A, see:
21. b) J. Simon, U. Bergsträsser, M. Regitz, K. K. Laali, Organometallics 1999, 18, 817-819;
22. c) F. G. N. Cloke, P. B. Hitchcock, J. F. Nixon, D. M. Vickers, C. R. Chim. 2004, 7, 931-940;
23. d) Gas phase reactivity of A: A. A. Sabino, M. N. Eberlin, L. A. B. Moraes, K. K. Laali, Org. Biomol. Chem. 2003, 1, 395-400.
24. Phosphiranylium ions were postulated as intermediates, see: e) E. Niecke, M. Leuer, M. Nieger, Chem. Ber. 1989, 122, 453-461;
25. f) W. W. Schoeller, W. Haug, J. Strutwolf, T. Bush, J. Chem. Soc. Faraday Trans. 1996, 92, 1751-1755.
26. a) M. Soleilhavoup, Y. Canac, A. M. Polozov, A. Baceiredo, G. Bertrand, J. Am. Chem. Soc. 1994, 116, 6149-6152;
27. b) D. Bourissou, G. Bertrand, Top. Curr. Chem. 2002, 220, 1-25.
28. J. Geier, G. Frison, H. Grtttzmacher, Angew. Chem. 2003, 115, 4085-4087;
29. Angew. Chem. Int. Ed. 2003, 42, 3955-3957.
30. J. Liedtke, S. Loss, G. Alcaraz, V. Gramlich, H. Grützmacher, Angew. Chem. 1999, 111, 1724-1727;
31. Angew. Chem. Int. Ed. 1999, 35, 1623-1626.
32. 3; see: J. Liedtke, S. Loss, Ch. Widauer, H. Grützmacher, Tetrahedron 2000, 56, 143-156.
33. 2.
34. CCDC 765756 (3) and 765757 (10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ datajequest/cif. For the experimental details of the X-ray crystal structure determinations, see the Supporting Information.
35. a) F. B. Läng, H. Grützmacher, Chimia 2003, 57,187-190;
36. b) J. Liedtke, Dissertation, ETH Zürich, Synthese und Koordinationschemie neuer polycyclischer Phosphirane, Nr. 13688, 2000.
37. Gaussian03 (RevisionC.02): M. J. Frisch, et al., see the Supporting Information.
38. a) R. F. W. Bader in Atoms in Molecules: a quantum theory (Ed. : R. F. W. Bader) Clarendon, Oxford, 1990;
39. b) P. L. Popelier in Atoms in Molecules: An Introduction (Ed.: P. L. Popelier), Prentice Hall, UK, 2000.
40. c)0; see: D. Cremer, E. Kraka,
41. Angew. Chem. 1984, 96, 612-614;
42. Angew. Chem. Int. Ed. Engl. 1984, 23, 627-628.
43. a) C. Chuit, C. Reyé, Eur. J. Inorg. Chem. 1998, 1847-1857;
44. b) M. Yoshifuji, S. Sangu, K. Kamijo, K. Toyota, Chem. Ber. 1996, 129, 1049-1055.
45. It is unclear whether exo-4 and endo-A are in a very slow equilibrium, (not detectable on the NMR time scale) through an inversion of the central ring or are formed through an attack of MeLi form either side on the P center.
46. L. R. Smith, J. L. Mills, J. Am. Chem. Soc. 1976, 95, 3852-3857.
47. a) S. C. Peake, R. Schmutzler, J. Chem. Soc. A 1970, 1049-1054;
48. b) A. I. Razumov, N. I. Sinitsyn, R. A. Salakhyt, N. N. Bankovsk, E. A. Krasilni, J. Gen. Chem. USSR 1972, 42, 1245-1248.
49. a) K. A. Petrov, G. I. Abramtseva, V P. Evdakov, A. K. Straut-man, J. Gen. Chem. USSR 1962, 32, 3019-3023;
50. b) T. König, W. D. Habicher, U. Hähner, J. Pionteck, C. Rüger, K. Schwetlick, J. Prakt. Chem. 1992, 334, 333-349.
51. Diphenyldisulfide is well known trapping agent for triplet phosphinidenes; see: a) U. Schmidt, C. Osterroht, Angew. Chem, 1965, 77, 455;
52. Angew. Chem. Int. Ed. Engl. 1965, 4, 437;
53. b) J. C. Slootweg, K. Lammertsma in Science of Synthesis, Vol. 42 (Eds.: B. M. Trost, F. Mathey), Georg Thieme, Stuttgart, 2009, pp. 15-36.
54. For NHC-stabilized phosphinidenes, see: a) A. J. Arduengo III, H. V. Rasika Dias, J. C. Calabrese, Chem. Lett. 1997, 143-144;
55. b) A. J. Arduengo III, J. C. Calabrese, A. H. Cowley, H. V. Rasika Dias, J. R. Goerlich, W. J. Marshall, B. Riegel, Inorg. Chem. 1997, 36, 2151-2158.
56. +, see: a) N. Kuhn, J. Fahl, D. Bläser, R. Boese, Z. Anorg. Allg. Chem. 1999, 625, 729-734;
57. b) B. D. Ellis, P. J. Ragogna, C. L. B. Macdonald, Inorg. Chem. 2004, 43, 7857-7867.
58. [14] using ADF2007.01, SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands, http://www.scm.com. See the Supporting Information for details.
59. a) B. D. Ellis, C. A. Dyker, A. Decken, C.L.B. Macdonald, Chem. Commun. 2005, 1965-1967;
60. see also: b) B. D. Ellis, C. L. B. Macdonald, Coord. Chem. Rev. 2007, 251, 936-973;
61. c) O. Back, G. Kuchenbeiser, B. Donnadieu, G. Bertrand, Angew. Chem. 2009, 121, 5638-5641;
62. Angew. Chem. Int. Ed. 2009, 48, 5530-5533.