Carbene and nitrene rearrangements: A theoretical study of cyclic allenes and carbenes, carbodiimides, and azirines

Journal of Organic Chemistry

Volumn 67, Issue 25, 2002, Pages 9023-9030

  Kuhn, Arvid ^a   Vosswinkel, Michael ^a   Wentrup, Curt ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ENERGY SURFACES;

INFRARED SPECTROSCOPY; PHOTOLYSIS;

AROMATIC COMPOUNDS;

ALLENE DERIVATIVE; AROMATIC COMPOUND; AZIRINE DERIVATIVE; CARBENE; CARBENOID; CYANAMIDE; HETEROCYCLIC COMPOUND; ISOQUINOLINE DERIVATIVE; NITROGEN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENERGY; INFRARED SPECTROSCOPY; MOLECULAR STABILITY; PHOTOLYSIS; RING CLOSING METATHESIS;

EID: 0037073875     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0258756     Document Type: Article

References (54)

1. (a) Wentrup, C. Top. Curr. Chem. 1976, 62, 173.
2. (b) Wentrup, C. Adv. Heterocycl. Chem. 1981, 28, 231.
3. (c) Platz, M. S. Acc. Chem. Res. 1995, 28, 487.
4. (d) Karney; W. L.; Borden, W. T. Adv. Carbene Chem. 2001, 3, 205.
5. (e) Gritsan, N. P.; Platz, M. S. Adv. Carbene Chem. 2001, 3, 255.
6. Crow, W. D.; Wentrup, C. Chem. Commun. 1969, 1387.
7. Wentrup, C.; Winter, H.-W. J. Am. Chem. Soc. 1980, 102, 6159.
8. Wentrup, C.; Thétaz, C.; Tagliaferri, E.; Lindner, H. J.; Kitschke, B.; Reisenauer, H. P.; Winter, H. W. Angew. Chem., Int. Ed. Engl. 1980, 19, 566.
9. Evans, R. A.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 4009.
10. Kuzaj, M.; Lüerssen, H.; Wentrup, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 480.
11. Reisinger, A.; Koch, R.; Wentrup, C. J. Chem. Soc., Perkin Trans. 1 1998, 2247.
12. (a) Matzinger, S.; Bally, T.; Patterson, E. V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535-1542.
13. (b) Wong, M. W.; Wentrup, C. J. Org. Chem. 1996, 61, 7022-7029.
14. (c) Schreiner, P. R.; Karney, W. L.; Schleyer, P. v. R.; Bordon, W. T.; Hamilton, T. P.; Schaefer, H. F., III J. Org. Chem. 1996, 61, 7030-7039.
15. (d) Karney, W. L.; Bordon, W. T. J. Am. Chem. Soc. 1997, 119, 1378-1387.
16. (e) Kemnitz, C. R.; Karney, W. L.; Bordon, W. T. J. Am. Chem. Soc. 1999, 120, 3499-3503.
17. (f) Geise, C. M.; Hadad, C. M. J. Org. Chem. 2002, 67, 2532.
18. Morawietz, J.; Sander, W. J. Org. Chem. 1996, 61, 4351.
19. West, P. R.; Mooring, A. M.; McMahon, R. J.; Chapman, O. L. J. Org. Chem. 1986, 51, 1316.
20. Becker, J.; Wentrup, C. J. Chem. Soc., Chem. Commun. 1980, 190.
21. Bonvallet, P. A.; McMahon, R. J. J. Am. Chem. Soc. 2000, 122, 9332.
22. (a) Albrecht, S. W.; McMahon, R. J. J. Am. Chem. Soc. 1993, 115, 855.
23. (b) Coburn, T. T.; Jones, W. M. J. Am. Chem. Soc. 1974, 96, 5218.
24. For cyclization of the analogous naphthylchlorocarbenes to cyclopropenes, see: Rempala; P.; Sheridan, R. S. J. Chem. Soc., Perkin Trans. 2, 1999, 2257.
25. Xie, Y.; Schreiner, P. R.; Schleyer, P. v. R.; Schaefer, H. F. J. Am. Chem. Soc. 1977, 119, 1370.
26. Wentrup, C.; Mayor, C.; Becker, J.; Lindner, H. J. Tetrahedron 1985, 41, 1601.
27. Dunkin, I. R.; Thomson, P. C. P. Chem. Commun. 1980, 499.
28. Kuhn, A.; Wentrup, C. Unpublished results. Zhendong, Z.; Platz, M. S.; Kuhn, A.; Vosswinkel, M.; Wentrup, C.; Bally, T. To be submitted for publication.
29. Kuhn, A.; Wentrup, C. Unpublished results. Zhendong, Z.; Platz, M. S.; Kuhn, A.; Vosswinkel, M.; Wentrup, C.; Bally, T. To be submitted for publication.
30. Vosswinkel, M.; Lüerssen, H.; Wentrup, C. To be submitted for publication. Vosswinkel, M. Ph.D Thesis, 2002, in preparation.
31. Vosswinkel, M.; Lüerssen, H.; Wentrup, C. To be submitted for publication. Vosswinkel, M. Ph.D Thesis, 2002, in preparation.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, revision E.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
33. Plüg, C.; Wallfisch, B.; Andersen, H. G.; Bernhardt, P. V.; Baker, L.-J.; Clark, G. R.; Wong, M. W.; Wentup, C. J. Chem. Soc., Perkin Trans. 2 2000, 2096. Kiselewsky, M.; Wentrup, C. Unpublished results.
34. Plüg, C.; Wallfisch, B.; Andersen, H. G.; Bernhardt, P. V.; Baker, L.-J.; Clark, G. R.; Wong, M. W.; Wentup, C. J. Chem. Soc., Perkin Trans. 2 2000, 2096. Kiselewsky, M.; Wentrup, C. Unpublished results.
35. Martin-Santamaria, S.; Lavan, B.; Rzepa, H., S. Chem. Commun. 2000, 1089. Martin-Santamaria, S.; Lavan, B.; Rzepa, H. S. J. Chem. Soc., Perkin Trans. 2 2000, 2372. Kastrup, G. J.; Oldfield, S. P.; Rzepa, H. S. Chem. Commun. 2002, 642.
36. Martin-Santamaria, S.; Lavan, B.; Rzepa, H., S. Chem. Commun. 2000, 1089. Martin-Santamaria, S.; Lavan, B.; Rzepa, H. S. J. Chem. Soc., Perkin Trans. 2 2000, 2372. Kastrup, G. J.; Oldfield, S. P.; Rzepa, H. S. Chem. Commun. 2002, 642.
37. Martin-Santamaria, S.; Lavan, B.; Rzepa, H., S. Chem. Commun. 2000, 1089. Martin-Santamaria, S.; Lavan, B.; Rzepa, H. S. J. Chem. Soc., Perkin Trans. 2 2000, 2372. Kastrup, G. J.; Oldfield, S. P.; Rzepa, H. S. Chem. Commun. 2002, 642.
38. Maier, G.; Endres, J. Chem. Eur. J. 1999, 5, 1590.
39. This behavior has been independently discovered by: Bonvallet, P. A.; Todd, E. M.; Kim, Y. S.; McMahon, R. J. J. Org. Chem. 2002, 67, 9031.
40. Reisinger, A.; Addicott, C.; Wentrup, C. Unpublished results. Addicott, C. Ph.D. Thesis, The University of Queensland, Brisbane, Australia, 2002.
41. Reisinger, A.; Addicott, C.; Wentrup, C. Unpublished results. Addicott, C. Ph.D. Thesis, The University of Queensland, Brisbane, Australia, 2002.
42. Mitschke, U.; Finnerty, J.; Addicott, C.; Lukosch, A.; Lan, N. M.; Wentrup, C. Manuscript in preparation.
43. Addicott, C.; Reisinger, A.; Wentrup, C. Unpublished results. Addicott, C. B.Sc. Honours Thesis, The University of Queensland, Brisbane, Australia 1998.
44. Addicott, C.; Reisinger, A.; Wentrup, C. Unpublished results. Addicott, C. B.Sc. Honours Thesis, The University of Queensland, Brisbane, Australia 1998.
45. Kaname, M.; Tsuchiya, T.; Sashida, H. Heterocycles 1999, 51, 2407.
46. Chapman, O. L.; LeRoux, J.-P. J. Am. Chem. Soc. 1978, 100, 282. Hayes, J. C.; Sheridan, R. S. J. Am. Chem. Soc. 1990, 112, 5879. Donnelly, T.; Dunkin, I. R.; Norwood, D. S. D.; Prentice, A.; Shields, C. J.; Thomson, P. C. P. J. Chem. Soc., Perkin Trans. 2 1985, 307.
47. Chapman, O. L.; LeRoux, J.-P. J. Am. Chem. Soc. 1978, 100, 282. Hayes, J. C.; Sheridan, R. S. J. Am. Chem. Soc. 1990, 112, 5879. Donnelly, T.; Dunkin, I. R.; Norwood, D. S. D.; Prentice, A.; Shields, C. J.; Thomson, P. C. P. J. Chem. Soc., Perkin Trans. 2 1985, 307.
48. Chapman, O. L.; LeRoux, J.-P. J. Am. Chem. Soc. 1978, 100, 282. Hayes, J. C.; Sheridan, R. S. J. Am. Chem. Soc. 1990, 112, 5879. Donnelly, T.; Dunkin, I. R.; Norwood, D. S. D.; Prentice, A.; Shields, C. J.; Thomson, P. C. P. J. Chem. Soc., Perkin Trans. 2 1985, 307.
49. Chapyshev, S. V.; Kuhn, A.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 2000, 122, 1572.
50. Chapman, O. L.; Sheridan, R. S. J. Am. Chem. Soc. 1979, 101, 3690. Chapman, O. L.; Sheridan, R. S.; LeRoux, J.-P. Recl. Trav. Chim. Pays-Bas 1979, 98, 335.
51. Chapman, O. L.; Sheridan, R. S. J. Am. Chem. Soc. 1979, 101, 3690. Chapman, O. L.; Sheridan, R. S.; LeRoux, J.-P. Recl. Trav. Chim. Pays-Bas 1979, 98, 335.
52. West, P. R.; Chapman, O. L.; LeRoux, J.-P. J. Am. Chem. Soc. 1982, 104, 1779.
53. Wong, M. W. Chem. Phys. Lett. 1996, 256, 391. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
54. Wong, M. W. Chem. Phys. Lett. 1996, 256, 391. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.