Sulfonyl esters 7. The second and third sequences in the Trithioorthoformate Reaction

Canadian Journal of Chemistry

Volumn 74, Issue 9, 1996, Pages 1638-1648

  Ginige, Kashyapa Ananda ^a   Goehl, John Edward ^a   Langler, Richard Francis ^a  

^a MOUNT ALLISON UNIVERSITY   (Canada)

Author keywords

Single electron transfer; Sulfenes; Sulfonate esters

Indexed keywords

CHARGE TRANSFER; CHEMICAL BONDS; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; DISSOCIATION; ELECTRON TRANSPORT PROPERTIES; HYDROLYSIS;

ARYL MERCAPTAN; SINGLE ELECTRON TRANSFER; SULFENES; SULFONYL ESTERS; TRITHIOORTHOFORMATE;

ESTERS;

EID: 0030230444     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-181     Document Type: Article

References (30)

1. J.C. Baum, K.A. Durkin, L. Precedo, S.B. O'Blenes, J.E. Goehl, R.F. Langler, G.K. MacCormack, and L.L. Smith. Can. J. Chem. 69, 2127 (1991), and references therein.
2. J.C. Baum, B.E. Black, L. Precedo, J.E. Goehl, and R.F. Langler. Can. J. Chem. 73, 444 (1995).
3. J.F. King and M. Aslam. Can. J. Chem. 57, 3278 (1979).
4. (a) K. Ogura, K. Ohtsuki, M. Nakamura, N. Yahata, K. Takahashi, and H. Iida. Tetrahedron Lett. 26, 2455 (1985);
5. (b) Y. Murata, K. Inomata, H. Kinoshita, and H. Kotake. Bull. Chem. Soc. Jpn. 56, 2539 (1983).
6. K. Ogura, T. Tsuruda, K. Takahashi, and H. Iida. Tetrahedron Lett. 27, 3665 (1986).
7. G.L. Roof and W.P. Tucker. J. Org. Chem. 33, 3333 (1968).
8. D.G. Kay, R.F. Langler, and J.E. Trenholm. Can. J. Chem. 57, 2185 (1979).
9. R.F. Langler and J.L. Steeves. Aust. J. Chem. 47, 1641 (1994).
10. (a) P. Rumpf and J. Sadet. Bull. Soc. Chim. Fr. 447 (1958);
11. (b) R.R. Coats and D.T. Gibson. J. Chem. Soc. 442 (1940).
12. F.G. Bordwell. Acc. Chem. Res. 21, 456 (1988).
13. J.F. King and R. Rathore. In The chemistry of sulphonic acids, esters and their derivatives. Edited by S. Patai and Z. Rappoport. Wiley, Chichester. 1991. pp. 697-766.
14. (a) J.F. King and R.P. Beatson. Tetrahedron Lett. 973 (1975);
15. (b) M.B. Davy, K.T. Douglas, J.S. Loran, A. Steltner, and A. Williams. J. Am. Chem. Soc. 99, 1196 (1977);
16. (c) C.J.M. Stirling. Acc. Chem. Res. 12, 198 (1979);
17. (d) M.J. Pregel and E. Buncel. J. Chem. Soc. Perkin Trans. 2, 307 (1991).
18. (a) H. Pritzkow, K. Rall, S. Reimann-Andersen, and W. Sundermeyer. Angew. Chem. Int. Ed. Engl. 29, 60 (1990);
19. (b) T. Kempe and T. Norin. Acta Chem. Scand. Ser B: 28, 609 (1974);
20. (c) U. Rheude and W. Sundermeyer. Chem. Ber. 118, 2208 (1985);
21. (d) R. Allmann, W. Hanefeld, M. Krestel, and B. Spangenberg. Angew. Chem. Int. Ed. Engl. 26, 1133 (1987);
22. (e) J.F. King and T. Durst. Can. J. Chem. 44, 819 (1966);
23. (f) J.F. King, E.G. Lewars, and L.T. Danks. Can. J. Chem. 50, 866 (1972).
24. J.C. Baum, J. Bolhassan, R.F. Langler, P.J. Pujol, and R.K. Raheja. Can. J. Chem. 68, 1450 (1990).
25. K.A. Durkin, R.F. Langler, and N.A. Morrison. Can. J. Chem. 66, 3070 (1988).
26. J.J.P. Stewart. J. Comput. Chem. 10, 209 (1989).
27. J.S. Grossert and R.F. Langler. Can. J. Chem. 55, 407 (1977).
28. (a) W. Stevens and A. van Es. Recl. Trav. Chim. Pays-Bas, 83, 863 (1964);
29. (b) P.C. Bax and W. Stevens. Recl. Trav. Chim. Pays-Bas, 89, 265 (1970);
30. (c) P. Strazzolini, A.G. Giumanini, and S. Cauci. Tetrahedron, 46, 1081 (1990).