Intermolecular reactions of foiled carbenes with N-H bonds: Evidence for an ylidic pathway

Journal of Organic Chemistry

Volumn 73, Issue 17, 2008, Pages 6551-6558

  Mieusset, Jean Luc ^a   Bespokoev, Alexander ^a   Pacar, Mirjana ^a   Abraham, Michael ^a   Arion, Vladimir B ^a   Brinker, Udo H ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENES; CHEMICAL EQUATIONS; H BONDS; INTERMOLECULAR REACTIONS;

CHEMICAL REACTIONS;

[ENDOTRICYCLO[6.2.1.0 2,7]UNDEC 9 EN 11 YLIDENE)ACETOHYDRAZIDE; AMINE; AZIRINE DERIVATIVE; AZOLINE; CARBENOID; DIETHYLAMINE; ENDOTRICYCLO[6.2.1.0 2.7]UNDEC 9 EN 11 YLIDENE; HYDRAZONE DERIVATIVE; HYDROGEN; IMINE; N,N DIETHYL 11 ANTI,ENDO TRICYCLO[6.2.1.0 2,7]UNDEC 9 EN 11 AMINE; NITROGEN; NORBORNEN 7 YLIDENE; ORGANIC SOLVENT; RAC 5 METHOXY 5 METHYLSPIRO(5H [1,3,4]OXADIAZOLE 2,11' ENDOTRICYCLO[6.2.1.0 2,7]UNDEC 9 ENE; SODIUM DERIVATIVE; TERTIARY AMINE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DECOMPOSITION; GAS; HYDROGEN BOND; MOLECULAR INTERACTION; PHOTOLYSIS; PREDICTION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION;

EID: 51549112272     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800802m     Document Type: Article

References (64)

1. Gleiter, R.; Hoffmann, R. J. Am. Chem. Soc. 1968, 90, 5457.
2. (a) Freeman, P. K. J. Am. Chem. Soc. 1998, 120, 1619.
3. (b) Freeman, P. K.; Pugh, J. K. J. Org. Chem. 2000, 65, 6107.
4. (c) Freeman, P. K.; Dacres, J. E. J. Org. Chem. 2003, 68, 1386.
5. (d) Mieusset, J.-L.; Brinker, U. H. J. Org. Chem. 2005, 70, 10572.
6. (e) Mieusset, J.-L.; Brinker, U. H. J. Org. Chem. 2006, 71, 6975.
7. (f) Mieusset, J.-L.; Brinker, U. H. J. Am. Chem. Soc. 2006, 128, 15843.
8. (g) Mieusset, J.-L.; Brinker, U. H. J. Org. Chem. 2007, 72, 263.
9. Moss, R. A.; Dolling, U.-H.; Whittle, J. R. Tetrahedron Lett. 1971, 12, 931.
10. (a) Brown, W. T.; Jones, W. M. J. Org. Chem. 1979, 44, 3090.
11. (b) Brinker, U. H.; Ritzer, J. J. Am. Chem. Soc. 1981, 103, 2116.
12. (c) Kirmse, W.; Chiem, P. V.; Henning, P. G. J. Am. Chem. Soc. 1983, 105, 1695.
13. (d) Brinker, U. H.; König, L. Chem. Lett. 1984, 45.
14. (e) Baird, M. S.; Jefferies, I. Tetrahedron Lett. 1986, 27, 2493.
15. (f) Fleischhauer, I.; Brinker, U. H. Chem. Ber. 1987, 120, 501.
16. (g) Jones, D. W.; Marmon, R. J. Tetrahedron Lett. 1989, 30, 5467.
17. (a) Fickes, G. N.; Rose, C. B. J. Org. Chem. 1972, 37, 2898.
18. (b) Fisch, M. H.; Pierce, H. D. J. Chem. Soc., Chem. Commun. 1970, 503.
19. (c) Kirmse, W.; Kopannia, S. J. Org. Chem. 1998, 63, 1178.
20. Mieusset, J.-L.; Brinker, U. H. J. Org. Chem. 2008, 73, 1553.
21. (a) Moss, R. A.; Dolling, U.-H. Tetrahedron Lett. 1972, 13, 5117.
22. (b) Alberti, J.; Siegfried, R.; Kirmse, W. Liebigs Ann. Chem. 1974, 1605.
23. (c) Moss, R. A.; Ho, C.-T. Tetrahedron Lett. 1976, 17, 1651.
24. (d) Kirmse, W.; Meinert, T. J. Chem. Soc., Chem. Commun. 1994, 1065.
25. Hoch, P. E. J. Org. Chem. 1961, 26, 2066.
26. Dauben, W. G.; Kellogg, M. S. J. Am. Chem. Soc. 1980, 102, 4456.
27. Cotsaris, E.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1984, 95.
28. Yang, R.-Y.; Dai, L.-X. J. Org. Chem. 1993, 58, 3381.
29. The oxygen atom but also the azo function of the oxadiazoline ring can be positioned above the double bond of 6.
30. (a) Majchrzak, M. W.; Békhazi, M.; Tse-Sheepy, I.; Warkentin, J. J. Org. Chem. 1989, 54, 1842.
31. (b) Warkentin, J. J. Chem. Soc., Perkin Trans. I 2000, 2161.
32. (c) Czardybon, W.; Warkentin, J.; Werstiuk, N. H. J. Org. Chem. 2005, 70, 8431.
33. (a) Kirmse, W. Eur. J. Org. Chem. 1998, 201.
34. (b) Hashmi, A. S. K. J. Prakt. Chem. 1999, 341, 600.
35. (c) May, J. A.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 12426.
36. Fernamberg, K.; Snoonian, J. R.; Platz, M. S. Tetrahedron Lett. 2001, 42, 8761.
37. (a) Curtius, T. J. Prakt. Chem. 1888, 38, 396.
38. For recent examples with electrophilic metal carbenes, see: (b) Moody, C. J. Angew. Chem., Int. Ed. 2007, 46, 9148.
39. (c) Baumann, L. K.; Mbuvi, H. M.; Du, G.; Woo, L. K. Organometallics 2007, 16, 3995.
40. (d) Lee, E. C.; Fu, G. C. J. Am. Chem. Soc. 2007, 129, 12066.
41. With nucleophilic carbenes: (e) Frey, G. D.; Lavallo, V.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. Science 2007, 316, 439.
42. Bordwell, F. G.; Drucker, G. E.; Fried, H. E. J. Org. Chem. 1981, 46, 632.
43. In this study, the description anti is given if the substituent is oriented away from the alkenic bridge in order to facilitate the comparison between the bicyclo[2.2.1]hept-2-ene and the tricyclo[6.2.1.02,7]undec-9-ene systems. According to the IUPAC Gold Book, the description anti should be used when the group is oriented away from the lowest numbered bridge.
44. anti are formed. Instead, acetylhydrazone 5 is isolated, a compound resulting from reduction of the azo group followed by tautomerization and ring opening. It has already been observed that amines are able to photoreduce azoalkanes; see, for example: Adam, W.; Moorthy, J. N.; Nau, W. M.; Scaiano, J. C. J. Am. Chem. Soc. 1997, 119, 6749.
45. s symmetry.
46. (a) Cieplak, A. S. Chem. Rev. 1999, 99, 1265.
47. (b) Brown, H. C.; Muzzio, J. J. Am. Chem. Soc. 1966, 88, 2811.
48. (c) Mehta, G.; Khan, F. A. Tetrahedron Lett. 1992, 33, 3065.
49. (d) Mehta, G.; Gunasekaran, G.; Gadre, S.; Shirsat, R. N.; Ganguly, B.; Chandrasekhar, J. J. Org. Chem. 1994, 59, 1953.
50. (a) Heard, G. L.; Frankcombe, K. E.; Yates, B. F. Aust. J. Chem. 1993, 46, 1375.
51. (b) Heard, G. L.; Yates, B. F. J. Org. Chem. 1996, 61, 7276.
52. (c) Makita, K.; Koketsu, J.; Ando, F.; Ninomiya, Y.; Koga, N. J. Am. Chem. Soc 1998, 120, 5764.
53. Pliego, J. R.; De Almeida, W. B. J. Phys. Chem. A 1999, 103, 3904.
54. Gaussian 03: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 2003.
55. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
56. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
57. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968.
58. Gilbert, T. M. J. Phys. Chem A 2004, 108, 2550.
59. Guner, V.; Khuong, K. S.; Leach, A. G.; Lee, P. S.; Bartberger, M. D.; Houk, K. N. J. Phys. Chem. A 2003, 107, 11445.
60. Mieusset, J.-L.; Brinker, U. H. J. Org. Chem. 2007, 72, 263.
61. (a) Mihovilovic, M. D.; Snajdrova, R.; Winninger, A.; Rudroff, F. Synlett 2005, 2751.
62. (b) Snajdrova, R.; Braun, I.; Bach, T.; Mereiter, K.; Mihovilovic, M. D. J. Org. Chem. 2007, 72, 9597.
63. (a) Müller, R. K.; Joos, R.; Felix, D.; Schreiber, J.; Wintner, C.; Eschenmoser, A. Org. Synth. 1988, 6, 56.
64. (b) Felix, D.; Wintner, C.; Eschenmoser, A. Org. Synth. 1988, 6, 679.