P=C bonds as building blocks for three- and four-membered heterocyclic cations: Synthesis, structures and mechanistic studies

Chemistry - A European Journal

Volumn 18, Issue 6, 2012, Pages 1674-1683

  Bates, Joshua I ^a   Gates, Derek P ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

multiple bonds; phosphaalkenes; phosphetanes; phosphiranes; phosphorus heterocycles

Indexed keywords

MULTIPLE BONDS; PHOSPHAALKENES; PHOSPHETANES; PHOSPHIRANES; PHOSPHORUS HETEROCYCLES;

PHOSPHORUS; PHOSPHORUS COMPOUNDS; SALTS;

SYNTHESIS (CHEMICAL);

EID: 84856353136     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101535     Document Type: Article

References (97)

1. R. C. Fischer, P. P. Power, Chem. Rev. 2010, 110, 3877
2. P. P. Power, Chem. Rev. 1999, 99, 3463.
3. F. Mathey, Angew. Chem. 2003, 115, 1616
4. Angew. Chem. Int. Ed. 2003, 42, 1578
5. K. B. Dillon, F. Mathey, J. F. Nixon, Phosphorus: The Carbon Copy: From Organophosphorus to Phospha-Organic Chemistry, Wiley, New York, 1998
6. F. Mathey, Acc. Chem. Res. 1992, 25, 90
7. R. Appel, in Multiple Bonds and Low Coordination in Phosphorus Chemistry (Eds.:, M. Regitz, O. J. Scherer,), Thieme, Stuttgart, 1990.
8. J. I. Bates, J. Dugal-Tessier, D. P. Gates, Dalton Trans. 2010, 39, 3151.
9. D. P. Gates, Top. Curr. Chem. 2005, 250, 107.
10. K. J. T. Noonan, B. H. Gillon, V. Cappello, D. P. Gates, J. Am. Chem. Soc. 2008, 130, 12876
11. B. H. Gillon, B. O. Patrick, D. P. Gates, Chem. Commun. 2008, 2161
12. K. J. T. Noonan, D. P. Gates, Macromolecules 2008, 41, 1961
13. K. J. T. Noonan, B. Feldscher, J. I. Bates, J. J. Kingsley, M. Yam, D. P. Gates, Dalton Trans. 2008, 4451
14. K. J. T. Noonan, B. O. Patrick, D. P. Gates, Chem. Commun. 2007, 3658
15. B. H. Gillon, K. J. T. Noonan, B. Feldscher, J. M. Wissenz, Z. M. Kam, T. Hsieh, J. J. Kingsley, J. I. Bates, D. P. Gates, Can. J. Chem. 2007, 85, 1045
16. K. J. T. Noonan, D. P. Gates, Angew. Chem. 2006, 118, 7429
17. Angew. Chem. Int. Ed. 2006, 45, 7271
18. C. W. Tsang, B. Baharloo, D. Riendl, M. Yam, D. P. Gates, Angew. Chem. 2004, 116, 5800
19. Angew. Chem. Int. Ed. 2004, 43, 5682
20. C. W. Tsang, M. Yam, D. P. Gates, J. Am. Chem. Soc. 2003, 125, 1480.
21. J. I. Bates, D. P. Gates, J. Am. Chem. Soc. 2006, 128, 15998.
22. C. W. Tsang, C. A. Rohrick, T. S. Saini, B. O. Patrick, D. P. Gates, Organometallics 2004, 23, 5913.
23. Phosphorus-Carbon Heterocyclic Chemistry: The Rise of a New Domain (Ed.:, F. Mathey,), Pergamon, Amsterdam, 2001
24. C. A. Dyker, N. Burford, Chem. Asian J. 2008, 3, 28
25. D. Bourissou, G. Bertrand, Top. Curr. Chem. 2002, 220, 1
26. R. Streubel, Coord. Chem. Rev. 2002, 227, 175
27. D. Bourissou, G. Bertrand, Acc. Chem. Res. 1999, 32, 561
28. F. Mathey, Chem. Rev. 1990, 90, 997.
29. T. Kato, H. Gornitzka, A. Baceiredo, W. W. Schoeller, G. Bertrand, Science 2000, 289, 754.
30. T. Kato, H. Gornitzka, A. Baceiredo, W. W. Schoeller, G. Bertrand, J. Am. Chem. Soc. 2002, 124, 2506.
31. S. Loss, C. Widauer, H. Rüegger, U. Fleischer, C. M. Marchand, H. Grützmacher, G. Frenking, Dalton Trans. 2003, 85.
32. D. Martin, A. Baceiredo, G. Bertrand, Eur. J. Inorg. Chem. 2004, 3533.
33. Diaziridium cations (F) have not been isolated, but have been postulated as reaction intermediates; see:, E. Schmitz, Angew. Chem. 1964, 76, 197
34. Angew. Chem. Int. Ed. Engl. 1964, 3, 333
35. I. Washington, K. N. Houk, A. Armstrong, J. Org. Chem. 2003, 68, 6497.
36. S. Goumri, Y. Leriche, H. Gornitzka, A. Baceiredo, G. Bertrand, Eur. J. Inorg. Chem. 1998, 1539
37. L. Weber, M. H. Scheffer, H. G. Stammler, B. Neumann, W. W. Schoeller, A. Sundermann, Organometallics 1999, 18, 4216
38. L. Weber, S. Uthmann, H. G. Stammler, B. Neumann, W. W. Schoeller, R. Boese, D. Blaser, Eur. J. Inorg. Chem. 1999, 2369
39. N. Merceron, A. Baceiredo, H. Gornitzka, G. Bertrand, Chem. Commun. 2002, 2250
40. V. P. Morgalyuk, P. V. Petrovskii, K. A. Lysenko, E. E. Nifant′ev, Russ. J. Gen. Chem. 2010, 80, 100.
41. H. Helten, M. Engeser, D. Gudat, R. Schilling, G. Schnakenburg, M. Nieger, R. Streubel, Chem. Eur. J. 2009, 15, 2602.
42. S. Fankel, H. Helten, G. von Frantzius, G. Schnakenburg, J. Daniels, V. Chu, C. Muller, R. Streubel, Dalton Trans. 2010, 39, 3472.
43. A. Espinosa, R. Streubel, Chem. Eur. J. 2011, 17, 3166.
44. E. Niecke, E. Symalla, Chimia 1985, 39, 320.
45. J. I. Bates, B. O. Patrick, D. P. Gates, New J. Chem. 2010, 34, 1660.
46. 3 cage compound which formally contains the type E moiety has been reported, however, the ring carbon possesses a zwitterionic Al substituent; see:, B. Breit, A. Hoffmann, U. Bergsträsser, L. Ricard, F. Mathey, M. Regitz, Angew. Chem. 1994, 106, 1541
47. Angew. Chem. Int. Ed. Engl. 1994, 33, 1491.
48. CRC Handbook of Chemistry and Physics, 84 th ed., (Ed.: D. R. Lide,), CRC, Boca Raton, 2003, Section 9.
49. N. Burford, C. A. Dyker, M. Lumsden, A. Decken, Angew. Chem. 2005, 117, 6352
50. Angew. Chem. Int. Ed. 2005, 44, 6196.
51. 2 moiety; see:, K. K. Laali, B. Geissler, M. Regitz, J. J. Houser, J. Org. Chem. 1995, 60, 47.
52. 2 moieties; see:, R. J. Baker, H. Bettentrup, C. Jones, Acta. Crystallogr. Sect. C 2003, 59, m 339.
53. 2 rings have been reported; see:, H.-P. Schrödel, A. Schmidpeter, Chem. Ber. 1997, 130, 1519.
54. B. Steger, H. Oberhammer, J. Grobe, D. Levan, Inorg. Chem. 1986, 25, 3177.
55. L. Heuer, L. Ernst, R. Schmutzler, D. Schomburg, Angew. Chem. 1989, 101, 1549
56. Angew. Chem. Int. Ed. Engl. 1989, 28, 1507.
57. S. D. Riegel, N. Burford, M. D. Lumsden, A. Decken, Chem. Commun. 2007, 4668.
58. J. J. Weigand, N. Burford, R. J. Davidson, S. Cameron, P. Seelheim, J. Am. Chem. Soc. 2009, 131, 17943.
59. L. Weber, Eur. J. Inorg. Chem. 2000, 2425.
60. 2 with HOTf; see:, D. Gudat, E. Niecke, B. Krebs, M. Dartmann, Chimia 1985, 39, 277.
61. K. K. Laali, B. Geissler, O. Wagner, J. Hoffmann, R. Armbrust, W. Eisfeld, M. Regitz, J. Am. Chem. Soc. 1994, 116, 9407
62. K. K. Laali, B. Geissler, M. Regitz, J. J. Houser, J. Org. Chem. 1995, 60, 6362
63. V. A. Jones, S. Sriprang, M. Thornton-Pett, T. P. Kee, J. Organomet. Chem. 1998, 567, 199
64. D. Gudat, A. Haghverdi, H. Hupfer, M. Nieger, Chem. Eur. J. 2000, 6, 3414
65. M. B. Abrams, B. L. Scott, R. T. Baker, Organometallics 2000, 19, 4944
66. S. L. Renard, T. P. Kee, J. Organomet. Chem. 2002, 643, 516.
67. D. C. R. Hockless, M. A. Mcdonald, M. Pabel, S. B. Wild, J. Chem. Soc. Chem. Commun. 1995, 257.
68. D. C. R. Hockless, M. A. McDonald, M. Pabel, S. B. Wild, J. Organomet. Chem. 1997, 529, 189.
69. N. E. Brasch, I. G. Hamilton, E. H. Krenske, S. B. Wild, Organometallics 2004, 23, 299.
70. K. Lammertsma, Top. Curr. Chem. 2003, 229, 95.
71. A. Igau, A. Baceiredo, H. Grützmacher, H. Pritzkow, G. Bertrand, J. Am. Chem. Soc. 1989, 111, 6853
72. H. Grützmacher, H. Pritzkow, Angew. Chem. 1992, 104, 92
73. Angew. Chem. Int. Ed. Engl. 1992, 31, 99
74. H. Grützmacher, H. Pritzkow, Angew. Chem. 1991, 103, 721
75. Angew. Chem. Int. Ed. Engl. 1991, 30, 709.
76. O. Guerret, G. Bertrand, Acc. Chem. Res. 1997, 30, 486.
77. + cannot be performed by simple methylation of a phosphinine; see:, A. Moores, L. Ricard, P. Le Floch, Angew. Chem. 2003, 115, 5090
78. Angew. Chem. Int. Ed. 2003, 42, 4940.
79. T. A. Van der knap, F. Bickelhaupt, Tetrahedron Lett. 1982, 23, 2037.
80. T. C. Klebach, R. Lourens, F. Bickelhaupt, J. Am. Chem. Soc. 1978, 100, 4886.
81. M. Yam, J. H. Chong, C. W. Tsang, B. O. Patrick, A. E. Lam, D. P. Gates, Inorg. Chem. 2006, 45, 5225
82. X.-G. Zhou, L.-B. Zhang, R.-F. Cai, Q.-J. Wu, L.-H. Weng, Z.-E. Huang, J. Organomet. Chem. 2000, 604, 260
83. M. Fild, P. G. Jones, K. Ruhnau, C. Thone, Z. Naturforsch. B: J. Chem. Sci. 1994, 49, 1361
84. L. N. Markovski, V. D. Romanenko, Tetrahedron 1989, 45, 6019
85. J. Grobe, D. Le Van, Angew. Chem. 1984, 96, 716
86. Angew. Chem. Int. Ed. Engl. 1984, 23, 710
87. G. Becker, W. Becker, O. Mundt, Phosphorus Sulfur Relat. Elem. 1983, 14, 267
88. G. Becker, W. Becker, G. Uhl, W. Uhl, H.-J. Wessely, Phosphorus Sulfur Relat. Elem. 1983, 18, 7
89. R. Appel, F. Knoll, I. Ruppert, Angew. Chem. 1981, 93, 771
90. Angew. Chem. Int. Ed. Engl. 1981, 20, 731
91. G. Becker, W. Uhl, H. J. Wessely, Z. Anorg. Allg. Chem. 1981, 479, 41.
92. G. M. Sheldrick, SAINT, Version 7.03A, Bruker AXS Inc., Madison, 1997.
93. G. M. Sheldrick, SADABS, Version 2.03, Bruker AXS Inc., Madison, 2001.
94. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115.
95. G. M. Sheldrick, SHELXTL, Version 5.1, Bruker AXS Inc., Madision, 1997.
96. R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797
97. Angew. Chem. Int. Ed. 1969, 8, 781.