Intramolecular reactions of dialkoxycarbenes with a carbonyl group

Canadian Journal of Chemistry

Volumn 81, Issue 6, 2003, Pages 598-606

  Dawid, Małgorzata ^a   Warkentin, John ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

"oxirane dimers"; Bicyclic ketone; Dialkoxycarbene; Dialkoxyoxirane; Hydroxylactone

Indexed keywords

ADDITION REACTIONS; BENZENE; CHEMICAL BONDS; HYDROLYSIS; KETONES; MOLECULAR STRUCTURE; X RAY DIFFRACTION ANALYSIS;

FUNCTIONAL GROUPS; METHANOLYSIS;

THERMOANALYSIS;

BENZENE; BICYCLO COMPOUND; CARBENE; CARBENOID; CARBON; CARBONYL DERIVATIVE; CATION; CYCLOPENTANONE DERIVATIVE; DIMER; ETHYLENE OXIDE DERIVATIVE; KETONE; LACTONE; METHANOL; OXADIAZOLE DERIVATIVE; WATER;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; GAS CHROMATOGRAPHY; HEAT TREATMENT; HYDROLYSIS; LYSIS; RING OPENING; X RAY DIFFRACTION;

EID: 0042734622     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v02-200     Document Type: Article

References (35)

1. (a) R.W. Hoffmann and H. Häuser. Tetrahedron, 21, 891 (1965);
2. (b) D.M. Lemal, E.P. Gosselink, and S.D. McGregor. J. Am. Chem. Soc. 88, 582 (1966);
3. (c) R.W. Hoffmann. Angew. Chem. Int. Ed. Engl. 10, 529 (1971);
4. (d) R.W. Hoffmann, K. Steinbach, and B. Dittrich. Chem. Ber. 106, 2174 (1973);
5. (e) R.W. Hoffmann and M. Reiffen. Chem. Ber. 109, 2565 (1976);
6. (f) R.A. Moss and J.K. Huselton. J. Chem. Soc., Chem. Commun. 950 (1976);
7. (g) G. Hömberger, W. Kirmse, and R. Lelgemann. Chem. Ber. 124, 1867 (1991);
8. (h) G. Frenzen, M. Rischke, and G. Seitz. Chem. Ber. 126, 2317 (1993);
9. (i) C. Gerninghaus, A. Kümmell, and G. Seitz. Chem. Ber. 126, 733 (1993);
10. (j) P. Couture, D.L. Pole, and J. Warkentin. J. Chem. Soc., Perkin Trans. 2, 1565 (1997);
11. (k) J. Warkentin. J. Chem. Soc., Perkin Trans. 1, 2161 (2000).
12. (a) R.A. Moss, C.B. Mallon, and C.-T. Ho. J. Am. Chem. Soc. 99, 4105 (1977);
13. (b) R.A. Moss. Acc. Chem. Res. 13, 58 (1980);
14. (c) R.A. Moss, C.M. Young, L.A. Perez, K. Krogh-Jespersen. J. Am. Chem. Soc. 103, 2413 (1981).
15. N.G. Rondan, K.N. Houk, and R.A. Moss. J. Am. Chem. Soc. 102, 1770 (1980).
16. N. Kuhn, J. Fahl, R. Boese, G. Henkel. Z. Naturforsch. 53b, 881 (1998).
17. J.A. Dunn, J.P. Pezacki, M.J. McGlinchey, and J. Warkentin. J. Org. Chem. 64, 4344 (1999).
18. J.P. Ross, P. Couture, and J. Warkentin. Can. J. Chem. 75, 1331 (1997).
19. (a) H.-W. Wanzlick. Angew. Chem. Int. Ed. Engl. 1, 75 (1962);
20. (b) G. Doleschall. Tetrahedron Lett. 21, 4183 (1980).
21. R.A. Braun. J. Am. Chem. Soc. 87, 5516 (1965).
22. D.L. Pole and J. Warkentin. J. Org. Chem. 62, 4065 (1997).
23. (a) M. Dawid, P.C. Venneri, and J. Warkentin. Can. J. Chem. 79, 110 (2001);
24. (b) M. Dawid, P.C. Venneri, and J. Warkentin. Can. J. Chem. 79, 1294 (2001).
25. D.L. Pole and J. Warkentin. Liebigs Ann. 1907 (1995).
26. P.C. Venneri and J. Warkentin. Can. J. Chem. 78, 1194 (2000).
27. M. Dawid, G. Mloston, and J. Warkentin. Org. Lett. 3, 2455 (2001).
28. N. Kuhn, H. Bohnen, and G. Henkel. Z. Naturforsch. 49b, 1473 (1994).
29. N. Kuhn, M. Steimann, and G. Weyers. Z. Naturforsch. 54b, 427 (1999).
30. N. Kuhn, K. Eichele, and M. Walker. Z. Anorg. Allg. Chem. 627, 2565 (2001).
31. D.L. Boger and C.E. Brotherton. Tetrahedron Lett. 25, 5611 (1984).
32. K. Kassam and J. Warkentin. J. Org. Chem. 59, 5071 (1994).
33. K. Kassam, D.L. Pole, M. El-Saidi, and J. Warkentin. J. Am. Chem. Soc. 116, 1161 (1994).
34. H.N.C. Wong. Houben-Weyl: Methods of organic chemistry. Vol. E17e. Edited by A. deMeijere. Georg Thieme Verlag, Stuttgart. 1998. pp. 513-514.
35. H.E. Zimmerman and J. English. J. Am. Chem. Soc. 76, 2285 (1954).