The hydroperoxysulfonium ylide. An aberration or a ubiquitous intermediate?

Tetrahedron

Volumn 62, Issue 46, 2006, Pages 10724-10728

  Clennan, Edward L ^a   Liao, Chen ^a  

^a UNIVERSITY OF WYOMING   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; ISOTOPE; SULFIDE; SULFONIUM DERIVATIVE; UBIQUITIN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL;

EID: 33749266742     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.111     Document Type: Article

References (21)

1. Oae S., and Doi J.T. Organic Sulfur Chemistry: Structure and Mechanism (1991), CRC, Boca Raton, FL p 433
2. Huang M.L., and Rauk A. J. Phys. Chem. A 108 (2004) 6222-6230
3. 2 Reaction Modes and Products. Part 2 (1985), CRC, Boca Raton, FL 1-117
4. Liang J.-J., Gu C.-L., Kacher M.L., and Foote C.S. J. Am. Chem. Soc. 105 (1983) 4717-4721
5. Clennan E.L. Sulfur Rep. 19 (1996) 171-214
6. Clennan E.L., Wang D., Clifton C., and Chen M.-F. J. Am. Chem. Soc. 119 (1997) 9081-9082
7. Clennan E.L., Wang D., Zhang H., and Clifton C.H. Tetrahedron Lett. 35 (1994) 4723-4726
8. Clennan E.L., Chen M.-F., Greer A., and Jensen F. J. Org. Chem. 63 (1998) 3397-3402
9. Clennan E.L., and Zhang H. J. Am. Chem. Soc. 116 (1994) 809-810
10. Greer A., Chen M.-F., Jensen F., and Clennan E.L. J. Am. Chem. Soc. 119 (1997) 4380-4387
11. Clennan E.L., and Chen M.-F. J. Org. Chem. 60 (1995) 6444-6447
12. Clennan E.L. Acc. Chem. Res. 34 (2001) 875-884
13. Jensen F., Greer A., and Clennan E.L. J. Am. Chem. Soc. 120 (1998) 4439-4449
14. Toutchkine A., and Clennan E.L. J. Org. Chem. 64 (1999) 5620-5625
15. The formation of an oxidative elimination product in the reactions of β-chlorosulfides also serves as experimental verification of hydroperoxysulfonium ylide intermediates. Toutchkine A., and Clennan E.L. Tetrahedron Lett. 40 (1999) 6519-6522
16. Aggarwal V.K., Schade S., and Adams H. J. Org. Chem. 62 (1997) 1139-1145
17. Clennan E.L., Wang D.-X., Yang K., Hodgson D.J., and Oki A.R. J. Am. Chem. Soc. 114 (1992) 3021-3027
18. Sheu C., Foote C.S., and Gu C.-L. J. Am. Chem. Soc. 114 (1992) 3015-3021
19. WINDNMR is an NMR simulation program written by Professor Hans Reich, University of Wisconsin, Madison. It is available at http://www.chem.wisc.edu/areas/reich/plt/windnmr.htm.
20. Clennan E.L., Hightower S.E., and Greer A. J. Am. Chem. Soc. 127 (2005) 11819-11826
21. Clennan E.L., and Hightower S.E. J. Org. Chem. 71 (2006) 1247-1250