Reactions of allyloxy(methoxy)carbene in solution. Carbene rearrangement and Claisen rearrangement of the carbene dimer

Tetrahedron

Volumn 61, Issue 24, 2005, Pages 5788-5796

  Plazuk, Damian ^a   Warkentin, John ^b   Werstiuk, Nick Henry ^b  

^a UNIVERSITY OF LODZ   (Poland)

^b MCMASTER UNIVERSITY   (Canada)

Author keywords

Allyloxy(methoxy)carbene; Carbene dimer; Claisen; Rearrangement

Indexed keywords

BENZENE; CARBENOID; DEUTERIUM; DIMER;

ARTICLE; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; PRIORITY JOURNAL; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 19744362248     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.04.024     Document Type: Article

References (33)

1. H. Iwamura, and H. Tukada Tetrahedron Lett. 1978 3451
2. H. Iwamura, M. Iwai, and H. Kihara Chem. Lett. 1977 881
3. J.E. Baldwin, and J.A. Walker J. Chem. Soc., Chem. Commun. 1972 354
4. R.W. Hoffmann, R. Hirsch, R. Fleming, and M.T. Reetz Chem. Ber. 105 1972 3532
5. P.C. Venneri, and J. Warkentin J. Am. Chem. Soc. 120 1998 11182
6. Addendum: J. Am. Chem. Soc. 121 1999 490
7. N. Merkley, P.C. Venneri, and J. Warkentin Can. J. Chem. 79 2001 312
8. K. Kassam, D.L. Pole, M. El-Saidi, and J. Warkentin J. Am. Chem. Soc. 116 1994 1161
9. R.L. Danheiser, J.J. Bronson, and K. Okano J. Am. Chem. Soc. 107 1985 4579
10. M.W. Majchrzak, and J. Warkentin Can. J. Chem. 67 1989 1753
11. A.P. Hitchcock, S. Zweep, T. Steel, M. Békhazi, and J. Warkentin Can. J. Chem. 60 1982 2914
12. N. Merkley, M. El-Saidi, and J. Warkentin Can. J. Chem. 78 2000 356
13. S. Marque, P.C. Le Mercier, P. Tordo, and H. Fischer Macromolecules 33 2000 4403
14. P.C. Venneri, and J. Warkentin Can. J. Chem. 78 2000 1194
15. F.E. Ziegler Chem. Rev. 88 1988 1423
16. P. Couture, M. El-Saidi, and J. Warkentin Can. J. Chem. 75 1997 326
17. C.-S. Ge, E.A. Jefferson, and R.A. Moss Tetrahedron Lett. 34 1993 7549
18. M. El-Saidi, K. Kassam, D.L. Pole, T. Tadey, and J. Warkentin J. Am. Chem. Soc. 114 1992 8751
19. R.A. Moss, M. Wlostowski, S. Shen, K. Krogh-Jespersen, and A. Matro J. Am. Chem. Soc. 110 1988 4443
20. J.W. Scheeren, R.J.F.M. Staps, and R.J.F. Nivard Recl. Trav. Chim. Pays-Bas 92 1973 11
21. R.W. Hoffmann, and H. Häuser Tetrahedron Lett. 1964 197
22. (a) 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.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 2003.
23. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1998 785
24. A.D. Becke J. Chem. Phys. 98 1993 5648
25. An analogous procedure for the generation of dimethoxy carbene at 40-50°C has been reported. H. Zhou, and J. Warkentin Org. Lett. 7 2005 487
26. W. Czardybon, A. Klys, J. Warkentin, and N.H. Werstiuk Can. J. Chem. 81 2003 1438
27. X. Lu, D.L. Reid, and J. Warkentin Can. J. Chem. 79 2001 319
28. H.-T. Er, D.L. Pole, and J. Warkentin Can. J. Chem. 74 1996 1480
29. K. Kassam, D.L. Pole, M. El-Saidi, and Warkentin J. Am. Chem. Soc. 116 1994 1161
30. J.W. Faller, C. Blankenship, B. Whitmore, and S. Sena Inorg. Chem. 24 1985 4483
31. W.C. Baird Jr., R.L. Hartgerink, and J.H. Surridge J. Org. Chem. 50 1985 4601
32. A.A.G. Shaikh, and S. Sivaram Ind. Eng. Chem. Res. 31 1992 1167
33. E.P. Woo, and F.C.W. Cheng J. Org. Chem. 51 1986 3704