Sulfanyl radical promoted C4′-C5′ bond scission of 5′-oxo-3′,4′-didehydro-2′,3′-dideoxynucleosides

Organic and Biomolecular Chemistry

Volumn 4, Issue 20, 2006, Pages 3754-3756

  Navacchia, Maria Luisa ^a   Montevecchi, Pier Carlo ^b  

^a CNR   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENETHIOL; DOUBLE BONDS; ELIMINATION REACTIONS; SULFANYL RADICALS;

ADDITION REACTIONS; ALDEHYDES; ALKALINITY; CATALYSIS; CHEMICAL BONDS; FURFURAL; REACTION KINETICS;

NUCLEIC ACIDS;

2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; FREE RADICAL; SOLVENT;

ARTICLE; CHEMISTRY; TEMPERATURE; TIME;

DIDEOXYNUCLEOSIDES; FREE RADICALS; SOLVENTS; TEMPERATURE; TIME FACTORS;

EID: 33749548037     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b609995e     Document Type: Article

References (22)

1. M. L. Navacchia C. Chatgilialoglu P. C. Montevecchi J. Org. Chem. 2006 71 4445
2. M. L. Navacchia A. Manetto P. C. Montevecchi C. Chatgilialoglu Eur. J. Org. Chem. 2005 4640
3. A. Romieu D. Gasparutto J. Cadet J. Chem. Soc., Perkin Trans. 1 1999 1257
4. T. Sugawara B. A. Otter T. Ueda Tetrahedron Lett. 1988 29 75
5. A. Kers T. Szabo J. Stawinski J. Chem. Soc., Perkin Trans. 1 1999 2585
6. S. Shuto M. Kanaaki S. Ichikawa N. Minakawa A. Matsuda J. Org. Chem. 1998 63 746
7. B. Giese P. Erdmann T. Schafer U. Schwitter Synthesis 1994 1310
8. A. K. Saha W. Schairer C. Waychunas C. V. C. Prasad M. Sardaro D. A. Upson L. I. Kruse Tetrahedron Lett. 1993 38 6017
9. S. Kralikova M. Budesinky M. Masojidkova I. Rosenberg Tetrahedron 2006 62 4917
10. L. S. Kappen I. H. Goldberg J. M. Liesch Proc. Natl. Acad. Sci. U. S. A. 1982 79 744
11. L. S. Kappen I. H. Goldberg Biochemistry 1983 22 4872
12. G. Pratviel M. Pitié C. Perigaud G. B. J. Gosselin B. Meunier J. Chem. Soc., Chem. Commun. 1993 149
13. G. Pratviel J. Bernadou B. Meunier Angew. Chem., Int. Ed. Engl. 1995 34 746
14. G. Pratviel M. Pitié J. Bernadou B. Meunier Angew. Chem., Int. Ed. Engl. 1991 30 702
15. V. Gotor F. Moris Synthesis 1992 626
16. J. A. Montgomery H. J. Thomas J. Org. Chem. 1981 46 594
17. 1H NMR and then chromatographed on a silica gel column by gradual elution with hexane-ethyl acetate.
18. We might explain this finding by assuming that polar factors could play a determining role, since both sulfanyl radicals and radicals 7a, b are expected to be electrophilic in character. In fact, it is generally assumed that the hydrogen atom transfer reaction is disfavored when the attacking radical and the displaced radical show the same philicity. See: B. P. Roberts A. J. Steel J. Chem. Soc., Perkin Trans. 2 1994 2155
19. B. P. Roberts J. Chem. Soc., Perkin Trans. 2 1996 2719
20. W. K. Pogozelski T. D. Tullius Chem. Rev. 1998 98 1089
21. M. Matsumoto J. Photochem. Photobiol., C 2004 5 27
22. N. Duran O. M. M. Faria Oliviera M. Haun G. Cilento J. Chem. Soc., Chem. Commun. 1977 442