The Role of Alkoxyl Radicals in Gif (GoAggv) Chemistry

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 823-826

  Snelgrove, Darren W ^a,b   MacFaul, Philip A ^a   Ingold, Keith U ^a   Wayner, Danial D M ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b CARLETON UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; OXIDE; RADICAL;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030067945     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02331-3     Document Type: Article

References (21)

1. Ortiz de Montellano, P. R. Ed. Cytochrome P-450: Structure, Mechanism and Biochemistry; Plenum: New York, 1986.
2. Lippard, S. J. Acc. Chem. Res. 1994, 27, 229-236.
3. Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504-512.
4. Dioxygen from the hydroperoxide, e.g., reaction 4, and from the air plays a role as a secondary oxidant, see, e.g., Knight, C.; Perkins, M. J. J. Chem. Soc., Chem. Commun. 1991, 925-927.
5. (a) Barton, D. H. R.; Chavasiri, W. Tetrahedron 1994, 50, 19-30.
6. (b) Barton, D. H. R.; Bévière, S D.; Chavasiri, W. Tetrahedron 1994, 50, 31-46.
7. Minisci, F.; Fontana, F.; Araneo, S.; Recupero, F. Tetrahedron Lett. 1994, 35, 3759-3762.
8. II catalysts under Gif conditions, see: (a) Bardin, C.; Barton, D. H. R.; Hu, B.; Rojas-Wahl, R.; Taylor, D. K. Tetrahedron Lett, 1994, 35, 5805-5808. (b) Barton, D. H. R.; Chabot, B. M.; Delanghe, N. C.; Hu, B.; Le Gloahec, V. N.; Rojas Wahl, R. U. Tetrahedron Lett 1995, 36, 7007-7010.
9. II catalysts under Gif conditions, see: (a) Bardin, C.; Barton, D. H. R.; Hu, B.; Rojas-Wahl, R.; Taylor, D. K. Tetrahedron Lett, 1994, 35, 5805-5808. (b) Barton, D. H. R.; Chabot, B. M.; Delanghe, N. C.; Hu, B.; Le Gloahec, V. N.; Rojas Wahl, R. U. Tetrahedron Lett 1995, 36, 7007-7010.
10. 3P was added to the remainding part of the mixture to convert all hydroperoxides to the corresponding alcohols, and then was followed by GC and GC/MS analysis.
11. Arends, I. W. C. E.; Ingold, K. U.; Wayner, D. D. M. J. Am. Chem. Soc. 1995, 117, 4710-4711.
12. PhC(O)OO• is ca. 860 times as reactive in H-atom abstraction as HOO•. See: Zaikov, G. E.; Howard, J. A.; Ingold, K. U. Can J. Chem. 1969, 47, 3017-3029.
13. -1 at 40°C in cyclopentane (see footnote 19 in ref. 12).
14. 16 are available in a number of pure solvents.
15. Avila, D. V.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1993, 115, 466-470.
16. β (and, hence, lifetimes) can be calculated for tert-butoxyl at 30°C.
17. Walling, C.; Wagner, P. J. J. Am. Chem. Soc. 1964, 86, 3368-3375.
18. (a) Minisci, F.; Fontana, F.; Araneo, S.; Recupero, F. J. Chem. Soc., Chem. Commun. 1994, 1823-1824.
19. (b) Minisci, F.; Fontana, F. Tetrahedron Lett. 1994, 35, 1427-1430.
20. (c) Minisci, F.; Fontana, F.; Araneo, S.; Recupero, F.; Banfi, S.; Quici, S. J. Am. Chem. Soc. 1995, 117, 226-232.
21. Newcomb, M.; Simakov, P. A.; Park, S.-U. accompying Letter in this issue.