Photooxygenation of alditol-1-C-yl derivatives of furan with singlet oxygen

Carbohydrate Research

Volumn 289, Issue , 1996, Pages 179-188

  Báñez Sanz, José Manuel ^a   Galisteo González, Diego ^a   López Sastre, Juan Antonio ^a   Rodríguez Amo, Justo Félix ^a   Romero Avila García, Cristina ^a   Santos García, Mercedes ^a   Sanz Tejedor, María Ascensión ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

alditol 1 C ylfuran derivatives; carbohydrate oxidation; furan derivatives; glycosuloses; sensitized photooxygenation

Indexed keywords

CARBOHYDRATE DERIVATIVE; FURAN DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHIRALITY; PHOTOCHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0342501969     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/0008-6215(96)00117-6     Document Type: Article

References (28)

1. R.A. Sheldon and J.K. Kochi, Metal-Catalyzed Oxidation of Organic Compounds, Academic Press, New York, 1981.
2. H.H. Wasserman and R.W. Murray (Eds.), Singlet Oxygen, Academic Press, New York, 1979.
3. (a) F. García González, Adv. Carbohydr. Chem., 11 (1956) 97-143;
4. (b) A. Gómez Sánchez and J. Fernández Bolaños, Adv. Carbohydr. Chem., 45 (1987) 7-20.
5. (a) G.O. Schenck, Angew. Chem., 56 (1944) 101-102;
6. (b) G.O. Schenck, Justus Liebigs Ann. Chem., 584 (1953) 156-176;
7. (c) M.R. Iesce, F. Cermola, A. Piazza, R. Scarpati, and M.L. Graziano, Synthesis (1995) 439-443.
8. B.H. Lipshutz, Chem. Rev., 86 (1986) 795-819.
9. B.L. Feringa, Recl. Trav. Chim. Pays-Bas, 106 (1987) 469-488.
10. C.W. Jefford and P.A. Cadby, Fortschr. Chem. Org. Naturst., 40 (1981) 191-265.
11. O. Hayaishi (Ed.), Molecular Mechanisms of Oxygen Activation, Academic Press, New York, 1974.
12. O. Achmatowicz, Jr., P. Bukowski, B. Szechner, Z. Zwierzchowska, and A. Zamojski, Tetrahedron, 27 (1971) 1973-1996.
13. O. Achmatowicz, Jr. and B. Szechner, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 19 (1971) 309-311.
14. C.S. Foote, M.T. Wuesthoff, S. Wexler, I.G. Burstain, R. Denny, G.O. Schenck, and K.H. Schulte-Elte, Tetrahedron, 23 (1967) 2583-2599.
15. (a) E. Koch and G.O. Schenck, Chem. Ber., 99 (1966) 1984-1990;
16. (b) G.O. Schenck and R. Appel, Naturwissenschaften, 33 (1946) 122-123.
17. P.A.J. Gorin, Can. J. Chem., 43 (1965) 2078-2084.
18. H. Zinner, H. Brandhoff, H. Schmandke, H. Kristen, and R. Haun, Chem. Ber., 92 (1959) 3151-3155.
19. F.J. López Aparicio, J.A. López Sastre, J. Molina Molina, and C. Romero-Avila García, An. Quim., 77 (1981) 348-350.
20. J.M. Báñez Sanz, D. Galisteo González, J.A. López Sastre, J.F. Rodríguez Amo, C. Romero-Avila García, M. Santos García, and M.A. Sanz Tejedor, An. Quim., 91 (1995) 399-406.
21. A. Gómez Sánchez, A. Rodríguez Roldán, and M. López Artíguez, An. Quim., Ser. B., 64 (1968) 507-514.
22. (a) H.H. Wasserman and A. Liberles, J. Am. Chem. Soc., 82 (1960) 2086-2086;
23. (b) R.E. Lutz, W.J. Welstead, Jr., R.G. Bass, and J.I. Dale, J. Org. Chem., 27 (1962) 1111-1112;
24. (c) T. Matsuura and I. Saito, Photochemistry of Heterocyclic Compounds, Wiley, N.Y., 1976, p. 456;
25. F.J. López Aparicio, J.A. López Sastre, J. Isac García, and R. Robles Díaz, Carbohydr. Res., 132 (1984) 19-27.
26. C. Dufraisse, G. Rio, and A. Ranjon, C. R. Acad. Sci. Paris, 264 (1967) 516-519.
27. A.M. Trozzolo and R.S. Fahrenholtz, Ann. N.Y. Acad. Sci., 171 (1970) 61-66.
28. B.C. Bera, A.B. Foster, and M. Stacey, J. Chem. Soc., (1956) 4531-4535.