Reactions of transition-metal η1-propargyl complexes with sulfur dioxide and sulfur trioxide: Transition-metal-carbon bond cleaving reactions of the cycloadducts which yield 1,2-oxathiole-2-oxides and -2,2-dioxides

Journal of Organometallic Chemistry

Volumn 598, Issue 1, 2000, Pages 150-159

  Hurley, Allison L ^a   Welker, Mark E ^a   Day, Cynthia S ^a  

^a WAKE FOREST UNIVERSITY   (United States)

Author keywords

Alkynyl complexes; Propargyl complexes; Sulfur heterocycles; 3+2 Cycloaddition

Indexed keywords

EID: 0001163642     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(99)00693-2     Document Type: Article

References (32)

1. For reviews of transition-metal mediated [3+2] cycloadditions see: (a) M.E. Welker, Chem. Rev. 92 (1992) 97.
2. (b) D.M.T. Chan, in: B.M. Trost (Ed.), Comprehensive Organic Syntheses, vol. 5, Pergamon, New York, 1991, p. 271.
3. (c) A. Wojcicki, Coord. Chem. Rev. 105 (1990) 35.
4. (d) M. Rosenblum, J. Organomet. Chem. 300 (1986) 191.
5. (a) B.L. Hayes, M.E. Welker, Organometallics 17 (1998) 5534.
6. (b) A.L. Hurley, M.E. Welker, C.S. Day, Organometallics 17 (1998) 2832.
7. (c) H.L. Stokes, L.M. Ni, J.A. Belot, M.E. Welker, J. Organomet. Chem. 487 (1995) 95.
8. (d) L.M. Ni, J.A. Belot, M.E. Welker, Tetrahedron Lett. 33 (1992) 177.
9. (e) M.E. Raseta, R.K. Mishra, S.A. Cawood, M.E. Welker, A.L. Rheingold, Organometallics 10 (1991) 2936.
10. (f) M.E. Raseta, S.A. Cawood, M.E. Welker, A.L. Rheingold, J. Am. Chem. Soc. 111 (1989) 8268.
11. Kensler T.W., Groopman J.D., Sutter T.R., Curphey T.J., Roebuck B.D. Chem. Res. Toxicol. 12:1999;113.
12. (a) M. Huang, A. Maynard, J.A. Turpin, L. Graham, G.M. Janini, D.G. Covell, W.G. Rice, J. Med. Chem. 41 (1998) 1371.
13. (b) W.G. Rice, D.C. Baker, C.A. Schaeffer, L. Graham, M. Bu, S. Terpening, D. Clanton, R. Schultz, J.P. Bader, R.W. Buckheit, L. Field, P.K. Singh, J.A. Turpin, Antimicrob. Agents Chemother. 41 (1997) 419. For a review see: W.G. Rice, J.A. Turpin, Rev. Med. Virol. 6 (1996) 187.
14. (b) W.G. Rice, D.C. Baker, C.A. Schaeffer, L. Graham, M. Bu, S. Terpening, D. Clanton, R. Schultz, J.P. Bader, R.W. Buckheit, L. Field, P.K. Singh, J.A. Turpin, Antimicrob. Agents Chemother. 41 (1997) 419. For a review see: W.G. Rice, J.A. Turpin, Rev. Med. Virol. 6 (1996) 187.
15. Williams J.P., Wojcicki A. Inorg. Chem. 16:1977;3116.
16. (a) J.L. Roustan, P. Cadiot, C.R. Acad. Sci. 268 (1969) 734.
17. (b) J.E. Thomasson, P.W. Robinson, D.A. Ross, A. Wojcicki, Inorg. Chem. 10 (1971) 2130.
18. Baudouy R., Delbecq F., Gore F. Tetrahedron. 36:1980;189.
19. (a) Z.Y. Yang, D.J. Burton, Tetrahedron 31 (1990) 1369.
20. (b) Y. Kondo, S. Kojima, T. Sakamoto, J. Org. Chem. 62 (1997) 6507.
21. Wadsworth D.H., Geer S.M., Detty M.R. J. Org. Chem. 52:1987;3662.
22. M.A. Harris, I. McMillan, J.H.C. Nayler, N.F. Osborne, M.J. Pearson, R. Southgate, J. Chem. Soc. Perkin Trans. I (1976) 1612.
23. W.D. Bannister, B.L. Booth, R.L. Haszeldine, P.L. Loader, J. Chem. Soc. A (1971) 930.
24. (a) D.W. Lichtenberg, A. Wojcicki, J. Organomet. Chem. 33 (1971) C77.
25. (b) D.W. Lichtenberg, A. Wojcicki, Inorg. Chim. Acta 7 (1973) 311.
26. (c) J.L. Roustan, J.Y. Merour, J. Benaim, C. Charrier, Acad. Sci. Ser. C 274 (1972) 537.
27. Dieter R.K., Sharma R.R., Ryan W. Tetrahedron Lett. 38:1997;783.
28. (a) R.M.J. Liskamp, H.J.M. Zeegers, H.C.J. Ottenheijm, J. Org. Chem. 46 (1981) 5408.
29. (b) F. Jung, N.K. Sharma, T. Durst, J. Am. Chem. Soc. 95 (1973) 3420.
30. (c) D.N. Harpp, S.M. Vines, J.P. Montillier, T.H. Chan, J. Org. Chem. 41 (1976) 3987.
31. (d) T.G. Squires, C.G. Venier, B.A. Hodgson, L.W. Chang, F.A. Davis, T.W. Panunto, J. Org. Chem. 46 (1981) 2373.
32. Ross D.A., Thomasson J.E., Wojcicki A., Churchill M.R., Wormald J. J. Am. Chem. Soc. 92:1970;1795.