(Alkylthio)- and (phenylthio)methoxycarbenes from oxadiazolines

Canadian Journal of Chemistry

Volumn 74, Issue 8, 1996, Pages 1480-1489

  Er, Hui Teng ^a   Pole, David L ^a   Warkentin, John ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

Nucleophilic; Oxadiazoline; Oxythiocarbene; Thermolysis

Indexed keywords

AROMATIC COMPOUNDS; BAND STRUCTURE; CHEMICAL BONDS; CONFORMATIONS; PYROLYSIS; SYNTHESIS (CHEMICAL);

METHOXYCARBENES; NUCLEOPHILIC REACTIONS; OXADIAZOLINES; THERMOLYSIS;

ORGANIC COMPOUNDS;

EID: 0030218432     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-165     Document Type: Article

References (47)

1. (a) C. Gerninghaus, A. Kummell, and G. Seitz. Chem. Ber. 126, 733 (1993);
2. (b) C.-S. Ge, E.A. Jefferson, and R.A. Moss. Tetrahedron Lett. 34, 7549 (1993);
3. (c) R.A. Moss, W. Liu, and C.-S. Ge. J. Phys. Org. Chem. 6, 376 (1993);
4. (d) R.A. Moss, E.G. Jang, H. Fan, M. Włostowski, and K. Krogh-Jespersen. J. Phys. Org. Chem. 5, 104 (1992);
5. (e) A.J. Arduengo III, H.V. Rasika Dias, R.L. Harlow, and M. Kline. J. Am. Chem. Soc. 114, 5530, 1992;
6. (f) G. Homberger, W. Kirmse, and R. Lelgemann. Chem. Ber. 124, 1867 (1991);
7. (g) 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. (h) R.A. Moss. Acc. Chem. Res. 22, 15 (1989);
9. (i) R. Bonneau, M.T.H. Liu, and R.V. Suresh. J. Phys. Chem. 93, 4802 (1989);
10. (j) R.A. Moss, M. Włostowski, S. Shen, K. Krogh-Jespersen, and A. Matro. J. Am. Chem. Soc. 110, 4443 (1988);
11. (k) R.A. Moss, S. Shen, and M. Włostowski. Tetrahedron Lett. 29, 6417 (1988);
12. (l) R.S. Sheridan, R.A. Moss, B.K. Wilk, S. Shen, M. Włostowski, M.A. Kesselmayer, R. Subramanian, G. Kmiecik-Lawrynowicz, and K. Krogh-Jespersen. J. Am. Chem. Soc. 110, 7563 (1988);
13. (m) R.A. Moss and J. Włostowska. Tetrahedron Lett. 29, 2559 (1988);
14. (n) R.A. Moss, S. Shen, L.M. Hadel, G. Kmiecik-Lawrynowicz, J. Włostoska, and K. Krogh-Jespersen. J. Am. Chem. Soc. 109, 4341 (1987);
15. (o) R.A. Moss, M. Włostowski, J. Terpinski, G. Kmiecik-Lawrynowicz, and K. Krogh-Jespersen. J. Am. Chem. Soc. 109, 3811 (1987);
16. (p) R.A. Moss, C.M. Young, L.A. Perez, and K. Krogh-Jespersen. J. Am. Chem. Soc. 103, 2413 (1981);
17. (q) R.A. Moss. Acc. Chem. Res. 13, 58 (1980);
18. (r) W.W. Schoeller. Tetrahedron Lett. 21, 1505 (1980);
19. (s) N.P. Smith and I.D.R. Stevens. J. Chem. Soc. Perkin Trans. 2, 1298 (1979);
20. (t) R.A. Moss, M. Fedorynski, and W.-C. Shieh. J. Am. Chem. Soc. 101, 4736 (1979);
21. (u) R.A. Moss, C.B. Mallon, and C.-T. Ho. J. Am. Chem. Soc. 99, 4105 (1977);
22. (v) M. Reiffen and R.W. Hoffman. Chem. Ber. 110, 37 (1977);
23. (w) R.A. Moss and J.K. Huselton. J. Chem. Soc. Chem. Commun. 950 (1976);
24. (x) R.W. Hoffmann. Angew. Chem. Int. Ed. Engl. 10, 529 (1971).
25. (a) M. El-Saidi, K. Kassam, D.L. Pole, T. Tadey, and J. Warkentin. J. Am. Chem. Soc. 114, 8751 (1992);
26. (b) R.W. Hoffmann, K. Steinbach, and B. Dittrich. Chem. Ber. 106, 2174 (1973);
27. (c) R.W. Hoffmann and M. Reiffen. Chem. Ber. 109, 2565 (1976).
28. D.L. Pole and J. Warkentin. Liebigs Ann. 1907 (1995).
29. (a) K. Kassam, D.L. Pole, M. El-Saidi, and J. Warkentin. J. Am. Chem. Soc. 116, 1161 (1994);
30. (b) 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).
31. (a) K. Kassam and J. Warkentin. J. Org. Chem. 59, 5071 (1994);
32. (b) W.W. Win, M. Kao, M. Eiermann, J.J. McNamara, F. Wudl, D.L. Pole, K. Kassam, and J. Warkentin. J. Org. Chem. 59, 5871 (1994).
33. J. Hine and A.W. Klueppel. J. Am. Chem. Soc. 96, 2924 (1974).
34. H.-T. Er, D.L. Pole, M. El-Saidi, and J. Warkentin. International Chemical Congress of Pacific Basin Societies, Honolulu, Dec. 1995. Paper no. 1224.
35. W.B. Smith. J. Org. Chem. 60, 7456 (1995).
36. R.W. Hoffmann, W. Lilienblum, and B. Dittrich. Chem. Ber. 107, 3395 (1974).
37. (a) D.L. Boger and C.E. Brotherton-Pleiss. In Advances in cycloaddition. Vol. 2. Edited by D.P. Curran. JAI Press, Greenwich, Conn. 1990. pp. 147-216;
38. (b) D.L. Boger and J. Wysocki, Jr. J. Org. Chem. 53, 3408 (1988);
39. (c) D.L. Boger, C.E. Brotherton, and G.I. Georg. Org. Synth. 65, 32 (1987);
40. (d) D.L. Boger and C.E. Brotherton. J. Am. Chem. Soc. 108, 6713 (1986);
41. (e) J. Am. Chem. Soc. 108, 6695 (1986);
42. (f) J. Org. Chem. 50, 3425 (1985);
43. (g) J. Am. Chem. Soc. 106, 805 (1984);
44. (h) D.L. Boger, C.E. Brotherton, and C.E. Georg. Tetrahedron Lett. 25, 5615 (1984).
45. F.G. Bordwell and H.E. Fried. J. Org. Chem. 56, 4218 (1991).
46. J.B. Fulton and J. Warkentin. Can. J. Chem. 65, 1177 (1987).
47. I. Fleming. Frontier orbitals and organic chemical reactions. Wiley-Interscience, New York. 1977.