Methoxy-(2-trimethylsilyl)ethoxycarbene. Reactions with Michael acceptors, with hydroxylic compounds, and with miscellaneous functional groups

Canadian Journal of Chemistry

Volumn 74, Issue 7, 1996, Pages 1335-1340

  Pole, David L ^a   Sharma, Pradeep K ^a   Warkentin, John ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

C H bonds; Dialkoxycarbene; Dialkoxyoxadiazoline; Insertion into O H; N phenylmaleimide; Rearrangement

Indexed keywords

AROMATIC COMPOUNDS; CHROMATOGRAPHY; HYDROGEN BONDS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGEN; PYROLYSIS; STOICHIOMETRY;

DELOCALIZATION; DIALKOXYCARBENE; DIALKOXYOXADIAZOLINE; DIMETHYL ACETYLENEDICARBOXYLATE; METHOXY TRIMETHYLSILYLETHOXYCARBENE; MICHAEL ACCEPTORS; PHENYLMALEIMIDE; REARRANGEMENT;

CHEMICAL REACTIONS;

EID: 0030196054     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-149     Document Type: Article

References (33)

1. M. El-Saidi, K. Kassam, D. L. Pole, T. Tadey, and J. Warkentin. J. Am. Chem. Soc. 114, 8751 (1992).
2. K. Kassam, D.L. Pole, M. El-Saidi, and J. Warkentin. J. Am. Chem. Soc. 116, 1161 (1994).
3. A. de Meijere, S.I. Kozhushkov, D.S. Yufit, R. Boese, T. Haumann, D.L. Pole, P.K. Sharma, and J. Warkentin. Liebigs Ann. 601 (1996).
4. (a) K. Kassam and J. Warkentin. J. Org. Chem. 59, 5071 (1994);
5. (b) R.A. Moss, W. Liu, and C.-S. Ge. J. Phys. Org. Chem. 6, 376 (1993);
6. (c) G. Hornberger, W. Kirmse, and R. Lelgemann. Chem. Ber. 124, 1867 (1991);
7. (d) X.-M. Du, H. Fan, J.L. Goodman, M.A. Kesselmayer, K. Krogh-Jespersen, J.A. LaVilla, R.A. Moss, S. Shen, and R.S. Sheridan. J. Am. Chem. Soc. 112, 1920 (1990);
8. (e) R.A. Moss, M. Wlostowski, S. Shen, K. Krogh-Jespersen, and A. Matro. J. Am. Chem. Soc. 110, 4443 (1988);
9. (f) R.A. Moss, S. Shen, and M. Wlostowski. Tetrahedron Lett. 29, 6417 (1988);
10. (g) R.A. Moss, M. Wlostowski, J. Terpinski, G. Kmiecik-Lawrynowicz, and K. Krogh-Jespersen. J. Am. Chem. Soc. 109, 3811 (1987);
11. (h) R.A. Moss, C.M. Young, L.A. Perez, and K. Krogh-Jespersen. J. Am. Chem. Soc. 103, 2413 (1981);
12. (i) R.A. Moss and J.K. Husselton. J. Chem. Soc. Chem. Commun. 950 (1976);
13. (j) R.W. Hoffmann and M. Reiffen. Chem. Ber. 109, 2565 (1976).
14. J.B. Lambert. Tetrahedron, 46, 2677 (1990).
15. (a) R.W. Hoffmann, K. Steinbach, and W. Lilienblum. Chem. Ber. 109, 1759 (1976);
16. (b) R.W. Hoffmann, W. Lilienblum, and B. Dittrich. Chem. Ber. 107, 3395 (1974);
17. (c) R.W. Hoffmann, K. Steinbach, and B. Dittrich. Chem. Ber. 106, 2174 (1973).
18. D.L. Boger and C.E. Brotherton-Pleiss. Advances in cycloaddition. Vol. 2. Edited by D.P. Curran. JAI Press, Greenwich, Conn. 1990. p. 147.
19. D.L. Boger and C.E. Brotherton. J. Am. Chem. Soc. 108, 6695 (1986).
20. D.L. Pole and J. Warkentin. Liebigs Ann. 1907 (1995).
21. (a) R. Scarpati, D. Sica, and C. Santacroce. Tetrahedron, 20, 2735 (1964);
22. (b) W.T. Brady and R.D. Watts. J. Org. Chem. 46, 4047 (1981).
23. (a) L. Tenud, S. Farooq, J. Seibl, and A. Eschenmoser. Helv. Chem. Acta, 53, 2059 (1970);
24. (b) J.F. King and M.J. McGarrity. J. Chem. Soc. Chem. Commun. 1140 (1979);
25. (c) E. Schaumann, T. Marr, H. Nimmesgern, and S. Sieveking. Chem. Ber. 120, 335 (1987);
26. (d) E. Schaumann, J. Dietz, E. Kausch, and G. C. Schmerse. Chem. Ber. 120, 339 (1987);
27. (e) J.E. Baldwin. J. Chem. Soc. Chem. Commun. 734 (1976).
28. T.L. Gilchrist and R.C. Storr. Organic reactions and orbital symmetry. Cambridge University Press, London. 1972.
29. (a) R.W. Hoffmann. Angew. Chem. Int. Ed. Engl. 18, 563 (1979);
30. (b) T. Nakai and K. Mikami. Chem. Rev. 86, 885 (1986);
31. (c) Y.-D. Wu and K.N. Houk. J. Org. Chem. 55, 1421 (1990).
32. (a) M.A. Cook, C. Eaborn, and D.R.M. Walton. J. Organomet. Chem. 24, 301 (1970);
33. (b) A.W.P. Jarvie, A. Holt, and J. Thompson. J. Chem. Soc. (B), 746 (1970).