Solid-state and electronic structure of benzoxazol-2-ylidene-triphenylborane complex

Organometallics

Volumn 15, Issue 1, 1996, Pages 452-455

  Lambert, Christoph ^a   Lopez Solera, Isabel ^b   Raithby, Paul R ^b  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000814143     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950427s     Document Type: Article

References (46)

1. (a) Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
2. (b) Arduengo, A. J.; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530.
3. (c) Regitz, M. Angew. Chem. 1991, 103, 691. For a stable triazolinylidene carbene, see: Enders, D.; Breuer, K.; Raabe, G.; Runsik, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. 1995, 107, 1119. Nucleophilic carbenes stabilized by two adjacent nitrogen atoms have been studied earlier by Wanzlick: Wanzlick, H. W.; Schikora, E. Angew. Chem. 1960, 72, 494; Chem. Ber. 1961, 94, 2389.
4. (c) Regitz, M. Angew. Chem. 1991, 103, 691. For a stable triazolinylidene carbene, see: Enders, D.; Breuer, K.; Raabe, G.; Runsik, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. 1995, 107, 1119. Nucleophilic carbenes stabilized by two adjacent nitrogen atoms have been studied earlier by Wanzlick: Wanzlick, H. W.; Schikora, E. Angew. Chem. 1960, 72, 494; Chem. Ber. 1961, 94, 2389.
5. (c) Regitz, M. Angew. Chem. 1991, 103, 691. For a stable triazolinylidene carbene, see: Enders, D.; Breuer, K.; Raabe, G.; Runsik, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. 1995, 107, 1119. Nucleophilic carbenes stabilized by two adjacent nitrogen atoms have been studied earlier by Wanzlick: Wanzlick, H. W.; Schikora, E. Angew. Chem. 1960, 72, 494; Chem. Ber. 1961, 94, 2389.
6. (c) Regitz, M. Angew. Chem. 1991, 103, 691. For a stable triazolinylidene carbene, see: Enders, D.; Breuer, K.; Raabe, G.; Runsik, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. 1995, 107, 1119. Nucleophilic carbenes stabilized by two adjacent nitrogen atoms have been studied earlier by Wanzlick: Wanzlick, H. W.; Schikora, E. Angew. Chem. 1960, 72, 494; Chem. Ber. 1961, 94, 2389.
7. (a) Arduengo, A. J.; Dias, H. V. R.; Calabrese, J. C.; Davidson, F. J. Am. Chem. Soc. 1992, 114, 9724.
8. (b) Kuhn, N.; Henkel, G.; Kratz, T.; Kreutzberg, J.; Boese, R.; Maulitz, A. H. Chem. Ber. 1993, 126, 2041.
9. (c) Arduengo, A. J.; Dais, Davidson, F.; H. V. R.; Harlow J. Organomet. Chem. 1993, 462, 13.
10. (d) Kuhn, N.; Kratz, T.; Bläser, D.; Boese, R. Chem. Ber. 1995, 128, 245.
11. (e) Arduengo, A. J.; Gamper, S. F.; Tamm, M.; Calabrese, J. C.; Davidson, F.; Craig, H. A. J. Am. Chem. Soc. 1995, 117, 572.
12. (f) Arduengo, A. J.; Tamm, M.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 3625.
13. (g) Arduengo, A. J.; Kline, M.; Calabrese, J. C.; Davidson, F. J. Am. Chem. Soc. 1991, 113, 9706.
14. (h) Arduengo, A. J.; Dias, H. V. R.; Calabrese, J. C.; Davidson, F. Inorg. Chem. 1993, 32, 1541.
15. (i) Kuhn, N.; Henkel, G.; Kratz, T. Chem. Ber. 1993, 126, 2047.
16. (j) Kuhn, N.; Bohnen, H.; Kreutzberg, J.; Bläser, D.; Boese, R. J. Chem. Soc., Chem. Commun. 1993, 1136.
17. (k) Kuhn, N.; Kratz, T.; Henkel, G. J. Chem. Soc., Chem. Commun. 1993, 1778.
18. (l) Williams, D. J.; Fawcett-Brown, M. R.; Raye, R. R.; VanDerveer, D.; Pang, Y. T.; Jones, R. L.; Bergbauer, K. L. Heteroat. Chem. 1993, 4, 409.
19. Houben-Weyl, Methoden der Organischen Chemie; Regitz, M., Ed.; Thieme: Stuttgart, 1989; Vol. E19b, pp 1765.
20. However, the solid-sttae structure of dimeric (4-tert-butylthiazolato)(glyme)lithium, which shows strong carbene character, has been published recently: Boche, G.; Hilf, C.; Harms, K.; Marsch, M.; Lohrenz, J. C. W. Angew. Chem. 1995, 107, 509.
21. Some recent examples: (a) Hahn, F. E.; Tamm, M. J. Organomet. Chem. 1993, 456, C11. (b) Hahn, F. E.; Tamm, M.; Lügger, T. Angew. Chem. 1994, 106, 1419. (c) Raubenheimer, H. G.; Cronje, S.; van Rooyen, P. H.; Olivier, P. J.; Toerien, J. G. Angew. Chem. 1994, 106, 687. (d) Raubenheimer, H. G.; Cronje, S.; Olivier, P. J. J. Chem. Soc., Dalton Trans. 1995, 313. (e) Hahn, F. E.; Tamm, M. J. Chem. Soc., Chem. Commun. 1993, 842.
22. Some recent examples: (a) Hahn, F. E.; Tamm, M. J. Organomet. Chem. 1993, 456, C11. (b) Hahn, F. E.; Tamm, M.; Lügger, T. Angew. Chem. 1994, 106, 1419. (c) Raubenheimer, H. G.; Cronje, S.; van Rooyen, P. H.; Olivier, P. J.; Toerien, J. G. Angew. Chem. 1994, 106, 687. (d) Raubenheimer, H. G.; Cronje, S.; Olivier, P. J. J. Chem. Soc., Dalton Trans. 1995, 313. (e) Hahn, F. E.; Tamm, M. J. Chem. Soc., Chem. Commun. 1993, 842.
23. Some recent examples: (a) Hahn, F. E.; Tamm, M. J. Organomet. Chem. 1993, 456, C11. (b) Hahn, F. E.; Tamm, M.; Lügger, T. Angew. Chem. 1994, 106, 1419. (c) Raubenheimer, H. G.; Cronje, S.; van Rooyen, P. H.; Olivier, P. J.; Toerien, J. G. Angew. Chem. 1994, 106, 687. (d) Raubenheimer, H. G.; Cronje, S.; Olivier, P. J. J. Chem. Soc., Dalton Trans. 1995, 313. (e) Hahn, F. E.; Tamm, M. J. Chem. Soc., Chem. Commun. 1993, 842.
24. Some recent examples: (a) Hahn, F. E.; Tamm, M. J. Organomet. Chem. 1993, 456, C11. (b) Hahn, F. E.; Tamm, M.; Lügger, T. Angew. Chem. 1994, 106, 1419. (c) Raubenheimer, H. G.; Cronje, S.; van Rooyen, P. H.; Olivier, P. J.; Toerien, J. G. Angew. Chem. 1994, 106, 687. (d) Raubenheimer, H. G.; Cronje, S.; Olivier, P. J. J. Chem. Soc., Dalton Trans. 1995, 313. (e) Hahn, F. E.; Tamm, M. J. Chem. Soc., Chem. Commun. 1993, 842.
25. Some recent examples: (a) Hahn, F. E.; Tamm, M. J. Organomet. Chem. 1993, 456, C11. (b) Hahn, F. E.; Tamm, M.; Lügger, T. Angew. Chem. 1994, 106, 1419. (c) Raubenheimer, H. G.; Cronje, S.; van Rooyen, P. H.; Olivier, P. J.; Toerien, J. G. Angew. Chem. 1994, 106, 687. (d) Raubenheimer, H. G.; Cronje, S.; Olivier, P. J. J. Chem. Soc., Dalton Trans. 1995, 313. (e) Hahn, F. E.; Tamm, M. J. Chem. Soc., Chem. Commun. 1993, 842.
26. (a) Jutzi, P.; Gilge, U. J. Organomet. Chem. 1983, 246, 159.
27. (b) Jacobi, P. A.; Ueng, S.; Carr, D. J. Org. Chem. 1979, 44, 2042.
28. (c) Hodges, C. J.; Patt, W. C.; Conolly, C. J. J. Org. Chem. 1991, 56, 449.
29. (d) Whitney, S. E.; Rickborn, B. J. J. Org. Chem. 1991, 56, 3058.
30. Odom, J. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, UK, 1982; Vol. 1, p 257.
31. (a) Fehlhammer, W. P.; Hoffmeister, H.; Boyadjiev, B.; Kolrep, T. Z. Naturforsch. 1989, 44B, 917.
32. (b) Fehlhammer, W. P.; Hoffineister, H.; Stolzenberg, H.; Boyadjiev, B. Z. Naturforsch. 1989, 44B, 419.
33. Erker, G.; Ahlers, W.; Fröhlich, R. J. Am. Chem. Soc. 1995, 117, 5853.
34. s) to be minima on the HF potential energy surface. GAUSSIAN 92: Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, R. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, G.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. P. P.; Pople, J. A. Gaussian Inc., Pittsburgh, PA, 1992. For a description of the basis set and methods, see: Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
35. s) to be minima on the HF potential energy surface. GAUSSIAN 92: Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, R. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, G.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. P. P.; Pople, J. A. Gaussian Inc., Pittsburgh, PA, 1992. For a description of the basis set and methods, see: Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
36. Ab initio calculations of a complex of imidazol-2-ylidene with borane have been reported previously: see ref 2b. For SCF-MO calculations of similar nucleophilic carbenes, see, e.g.: (a) Gleiter, R.; Hoffmann, R. J. Am. Chem. Soc. 1968, 90, 5457. (b) Sorensen, H. C.; Ingraham, L. L. J. Heterocycl. Chem. 1971, 8, 551. (c) Dixon, D. A.; Arduengo, A. J. J. Phys. Chem. 1991, 95, 4180. (d) Arduengo, A. J.; Dias, H. V. R.; Dixon, D. A.; Harlow, R. L.; Klooster, W. T.; Koetzle, T. F. J. Am. Chem. Soc. 1994, 116, 6812. (e) Sauers, R. R. Tetrahedron Lett. 1994, 35, 7213.
37. Ab initio calculations of a complex of imidazol-2-ylidene with borane have been reported previously: see ref 2b. For SCF-MO calculations of similar nucleophilic carbenes, see, e.g.: (a) Gleiter, R.; Hoffmann, R. J. Am. Chem. Soc. 1968, 90, 5457. (b) Sorensen, H. C.; Ingraham, L. L. J. Heterocycl. Chem. 1971, 8, 551. (c) Dixon, D. A.; Arduengo, A. J. J. Phys. Chem. 1991, 95, 4180. (d) Arduengo, A. J.; Dias, H. V. R.; Dixon, D. A.; Harlow, R. L.; Klooster, W. T.; Koetzle, T. F. J. Am. Chem. Soc. 1994, 116, 6812. (e) Sauers, R. R. Tetrahedron Lett. 1994, 35, 7213.
38. Ab initio calculations of a complex of imidazol-2-ylidene with borane have been reported previously: see ref 2b. For SCF-MO calculations of similar nucleophilic carbenes, see, e.g.: (a) Gleiter, R.; Hoffmann, R. J. Am. Chem. Soc. 1968, 90, 5457. (b) Sorensen, H. C.; Ingraham, L. L. J. Heterocycl. Chem. 1971, 8, 551. (c) Dixon, D. A.; Arduengo, A. J. J. Phys. Chem. 1991, 95, 4180. (d) Arduengo, A. J.; Dias, H. V. R.; Dixon, D. A.; Harlow, R. L.; Klooster, W. T.; Koetzle, T. F. J. Am. Chem. Soc. 1994, 116, 6812. (e) Sauers, R. R. Tetrahedron Lett. 1994, 35, 7213.
39. Ab initio calculations of a complex of imidazol-2-ylidene with borane have been reported previously: see ref 2b. For SCF-MO calculations of similar nucleophilic carbenes, see, e.g.: (a) Gleiter, R.; Hoffmann, R. J. Am. Chem. Soc. 1968, 90, 5457. (b) Sorensen, H. C.; Ingraham, L. L. J. Heterocycl. Chem. 1971, 8, 551. (c) Dixon, D. A.; Arduengo, A. J. J. Phys. Chem. 1991, 95, 4180. (d) Arduengo, A. J.; Dias, H. V. R.; Dixon, D. A.; Harlow, R. L.; Klooster, W. T.; Koetzle, T. F. J. Am. Chem. Soc. 1994, 116, 6812. (e) Sauers, R. R. Tetrahedron Lett. 1994, 35, 7213.
40. Ab initio calculations of a complex of imidazol-2-ylidene with borane have been reported previously: see ref 2b. For SCF-MO calculations of similar nucleophilic carbenes, see, e.g.: (a) Gleiter, R.; Hoffmann, R. J. Am. Chem. Soc. 1968, 90, 5457. (b) Sorensen, H. C.; Ingraham, L. L. J. Heterocycl. Chem. 1971, 8, 551. (c) Dixon, D. A.; Arduengo, A. J. J. Phys. Chem. 1991, 95, 4180. (d) Arduengo, A. J.; Dias, H. V. R.; Dixon, D. A.; Harlow, R. L.; Klooster, W. T.; Koetzle, T. F. J. Am. Chem. Soc. 1994, 116, 6812. (e) Sauers, R. R. Tetrahedron Lett. 1994, 35, 7213.
41. Jonas, V.; Frenking, G.; Reetz, M. T. J. Am. Chem. Soc. 1994, 116, 8741.
42. (a) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 753.
43. (b) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
44. (a) Taylor, T. E.; Hall, M. B. J. Am. Chem. Soc. 1984, 106, 1576.
45. (b) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissl, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Weinheim, Germany, 1983; p 113.
46. Similar arguments hold true for the methylene carbene and the imidazol-2-ylidene carbene and their protonated derivatives: see ref 11c.