Unusual rearrangements of 2-aroylimidoyl-2-phenylethylidene to 2,5- disubstituted oxazoles

Tetrahedron

Volumn 55, Issue 12, 1999, Pages 3637-3648

  Clark, Adrian D ^a   Janowski, Wit K ^a   Prager, Rolf H ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

2 AROYLIMIDOYL 2 PHENYLETHYLIDENE; OXAZOLE DERIVATIVE; OXAZOLONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL LABELING; CHEMICAL MODIFICATION; CHEMICAL REACTION; MOLECULAR DYNAMICS; MOLECULAR MODEL; MOLECULAR STABILITY; PRIORITY JOURNAL; PYROLYSIS; RADIOISOTOPE DISTRIBUTION; REACTION ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 0033582977     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01171-5     Document Type: Article

References (33)

1. Ang, K.H.; Prager, R.H.; Smith, J.A.; Weber, B.; Williams, C.M. Tetrahedron Lett., 1996, 37, 675-678.
2. Prager, R.H.; Smith, J.A.; Weber, B.; Williams, C.M. J. Chem. Soc. Perkin Trans, 1, 1997, 2665-2672.
3. Gilchrist, T.L.; Rees, C.W. Carbenes, Nitrenes and Arenes, Thomas Nelson: London 1969; Coyle, J.D. Photochemistry in Organic Synthesis, The Royal Society of Chemistry: London 1986.
4. Gilchrist, T.L.; Rees, C.W. Carbenes, Nitrenes and Arenes, Thomas Nelson: London 1969; Coyle, J.D. Photochemistry in Organic Synthesis, The Royal Society of Chemistry: London 1986.
5. Gilchrist, T.L.; Gymer, G.E.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1973, 555-556; Gilchrist, T.L., Gymer, G.E.; Rees, C.W. J. Chem. Soc. Perkin Trans. 1, 1975, 1-8; Gilchrist, T.L.; Rees, C.W.; Thomas, C. J. Chem. Soc., Perkin Trans. 1, 1975, 8-11; Mitchell, G.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1987, 413-422.
6. Gilchrist, T.L.; Gymer, G.E.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1973, 555-556; Gilchrist, T.L., Gymer, G.E.; Rees, C.W. J. Chem. Soc. Perkin Trans. 1, 1975, 1-8; Gilchrist, T.L.; Rees, C.W.; Thomas, C. J. Chem. Soc., Perkin Trans. 1, 1975, 8-11; Mitchell, G.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1987, 413-422.
7. Gilchrist, T.L.; Gymer, G.E.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1973, 555-556; Gilchrist, T.L., Gymer, G.E.; Rees, C.W. J. Chem. Soc. Perkin Trans. 1, 1975, 1-8; Gilchrist, T.L.; Rees, C.W.; Thomas, C. J. Chem. Soc., Perkin Trans. 1, 1975, 8-11; Mitchell, G.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1987, 413-422.
8. Gilchrist, T.L.; Gymer, G.E.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1973, 555-556; Gilchrist, T.L., Gymer, G.E.; Rees, C.W. J. Chem. Soc. Perkin Trans. 1, 1975, 1-8; Gilchrist, T.L.; Rees, C.W.; Thomas, C. J. Chem. Soc., Perkin Trans. 1, 1975, 8-11; Mitchell, G.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1987, 413-422.
9. Prager, R.H.; Singh, Y. Aust. J. Chem., 1994, 47, 1263-1270.
10. Sato, T.; Yamamoto, K.; Fukui, K.; Saito, K.; Hayakawa, K.; Yoshiie, S. J. Chem. Soc., Perkin Trans. 1, 1976, 783-787; Maeda, M.; Kojima, M. J. Chem. Soc., Perkin Trans. 1, 1977, 239-247.
11. Sato, T.; Yamamoto, K.; Fukui, K.; Saito, K.; Hayakawa, K.; Yoshiie, S. J. Chem. Soc., Perkin Trans. 1, 1976, 783-787; Maeda, M.; Kojima, M. J. Chem. Soc., Perkin Trans. 1, 1977, 239-247.
12. Kirmse, W.; Chiem, P.V.; Henning, P.G. J. Am. Chem. Soc., 1983, 105, 1695-1696. Carbene-carbene rearrangements occur most commonly by the Skattebol rearrangement, Holm, K.H.; Skattebol, L. Tetrahedron Lett., 1977, 2347-2350.
13. Kirmse, W.; Chiem, P.V.; Henning, P.O. J. Am. Chem. Soc., 1983, 705, 1695-1696. Carbene-carbene rearrangements occur most commonly by the Skattebol rearrangement, Holm, K.H.; Skattebol, L. Tetrahedron Lett., 1977, 2347-2350.
14. Rathke, M. W.; Deitch, J. Tetrahedron Lett., 1971, 2953-2956.
15. Prager, R.H.; Smith, J.A.; Weber, B.; Williams, C.M. J. Chem. Soc., Perkin Trans, 1, 1997, 2659-2664.
16. Closs, G.L.; Larrabee, R.B. Tetrahedron Lett., 1965, 287-296.
17. Anderson, D.J.; Gilchrist, T.L.; Gymer, G.E.; Rees, C.W., J. Chem. Soc., Chem. Commun., 1971, 1518.
18. Ab Initio Calculations Using Gaussian 94, Revision D.4, Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Gill, P.M.W.; Johnson, B.C.; 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, Inc.: Pittsburgh, 1995.
19. Seminario, J.M., (ed.), Recent Developments and Applications of Modern Density Functional Theory, Elsevier: New York 1996.
20. Carpenter, B.K. American Scientist, 1997, 85, 138-149; Carpenter, B.K. J. Am. Chem. Soc., 1996, 118, 10329-10330.
21. Carpenter, B.K. American Scientist, 1997, 85, 138-149; Carpenter, B.K. J. Am. Chem. Soc., 1996, 118, 10329-10330.
22. Horvat, D.A.; Fang, S.; Borden, W.T.; Carpenter, B.K. J. Am. Chem. Soc., 1997, 119, 5253-5254. Reyes, M.B.; Carpenter, B.K., J. Am. Chem. Soc., 1998, 120, 1641-1642.
23. Horvat, D.A.; Fang, S.; Borden, W.T.; Carpenter, B.K. J. Am. Chem. Soc., 1997, 119, 5253-5254. Reyes, M.B.; Carpenter, B.K., J. Am. Chem. Soc., 1998, 120, 1641-1642.
24. Ang, K.H.; Prager, R.H. Tetrahedron Lett., 1992, 33, 2845-2846.
25. Prager, R.H.; Singh, Y. Aust. J. Chem. 1992, 45, 1811-1823.
26. McNab, H.; Withell, K. Tetrahedron, 1996, 52, 3163-3170.
27. Posner, T. Ber. Dtsch. Chem. Ges., 1906, 39, 3515-3529.
28. Hammar, W.J.; Rustad, M.A. J. Heterocycl. Chem., 1981, 18, 885-888.
29. Hayes, F.N.; Rogers, B.S.; Ott, D.G. J. Am. Chem. Soc., 1955, 71,1850-1852
30. Gabriel, S. Ber. Dtsch. Chem. Ges., 1910, 43, 134-138; Ber. Dtsch. Chem. Ges., 1910, 43, 1283-1287.
31. Gabriel, S. Ber. Dtsch. Chem. Ges., 1910, 43, 134-138; Ber. Dtsch. Chem. Ges., 1910, 43, 1283-1287.
32. Houwing, H.A.; Wildeman, J.; Van Leusen, A.M. J. Heterocycl. Chem., 1981, 18, 1133-1139.
33. Minovici, S.S. Ber. Dtsch. Chem. Ges., 1896, 29, 2097-2106.