Trapping of peroxidic intermediates with sulfur and phosphorus centered electrophiles

Heteroatom Chemistry

Volumn 9, Issue 1, 1998, Pages 51-56

  Clennan, Edward L ^a   Stensaas, Kristina L ^a   Rupert, Sally D ^a  

^a UNIVERSITY OF WYOMING   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006794037     PISSN: 10427163     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-1071(1998)9:1<51::AID-HC6>3.0.CO;2-5     Document Type: Article

References (17)

1. E. L. Clennan, Tetrahedron, 47, 1991, 1343-1382.
2. E. L. Clennan, C. S. Foote: in W. Ando (ed): Organic Peroxides, Wiley, New York, pp. 255-318 (1992).
3. E. L. Clennan: in A. L. Baumstark (ed): Advances in Oxygenated Processes, JAI Press, Greenwich, CT, Vol. IV, pp. 49-80 (1995).
4. 4 + 2 Cycloadditions of singlet oxygen have often been referred to as concerted reactions; however, suggestions have been made that these reactions might proceed via exciplexes ([E. L. Clennan, M. E. Mehrsheik-Mohammadi, J. Am. Chem. Soc., 106, 1984, 7112-7118) or even perepoxide intermediates (K. M. Davis, B. K. Carpenter, J. Org. Chem. 61, 1996, 4617-4622; G. Delogu, D. Fabbri, F. Fabris, F. Sbrogiò, G. Valle, O. De Lucchi, J. Chem. Soc. Chem. Commun. 1995, 1887-1888).
5. 4 + 2 Cycloadditions of singlet oxygen have often been referred to as concerted reactions; however, suggestions have been made that these reactions might proceed via exciplexes ([E. L. Clennan, M. E. Mehrsheik-Mohammadi, J. Am. Chem. Soc., 106, 1984, 7112-7118) or even perepoxide intermediates (K. M. Davis, B. K. Carpenter, J. Org. Chem. 61, 1996, 4617-4622; G. Delogu, D. Fabbri, F. Fabris, F. Sbrogiò, G. Valle, O. De Lucchi, J. Chem. Soc. Chem. Commun. 1995, 1887-1888).
6. 4 + 2 Cycloadditions of singlet oxygen have often been referred to as concerted reactions; however, suggestions have been made that these reactions might proceed via exciplexes ([E. L. Clennan, M. E. Mehrsheik-Mohammadi, J. Am. Chem. Soc., 106, 1984, 7112-7118) or even perepoxide intermediates (K. M. Davis, B. K. Carpenter, J. Org. Chem. 61, 1996, 4617-4622; G. Delogu, D. Fabbri, F. Fabris, F. Sbrogiò, G. Valle, O. De Lucchi, J. Chem. Soc. Chem. Commun. 1995, 1887-1888).
7. E. L. Clennan, K. Yang, J. Org. Chem., 57, 1992, 4477-4487.
8. E. L. Clennan, A. Greer, J. Org. Chem., 61, 1996, 4793-4797.
9. T. Akasaka, A. Sakurai, W. Ando, J. Am. Chem. Soc., 113, 1991, 2696-2701.
10. K. Nahm, C. S. Foote, J. Am. Chem. Soc., 111, 1989, 1909-1910.
11. M. Stratakis, M. Orfanopoulos, C. S. Foote, Tetrahedron Lett., 32, 1991, 863-866.
12. J.-J. Liang, C.-L. Gu, M. L. Kacher, C. S. Foote, J. Am. Chem. Soc., 105, 1983, 4717-4721.
13. E. L. Clennan, M.-F. Chen, G. Xu, Tetrahedron Lett., 37, 1996, 2911-2914.
14. P. D. Bartlett, Chem. Soc. Rev., 5, 1976, 149-163.
15. M. P. Fleming, J. E. McMurray: in O. L. Chapman (ed): Organic Synthesis, John Wiley & Sons, Inc. Vol. 60, pp. 113-117 (1982).
16. E. L. Clennan, H. Zhang, J. Am. Chem. Soc., 117, 1995, 4218-4227.
17. D. J. Pasto, F. Cottard, S. Horgan, J. Org. Chem., 58, 1993, 4110-4112.