Oxidation of chiral 1,4-cyclohexadienes: A comparison of chemically and photochemically generated singlet oxygen 1O2 (1Δg)

Photochemistry and Photobiology

Volumn 70, Issue 4, 1999, Pages 524-530

  Nardello, V ^a   Aubry, J M ^a,c   Linker, T ^b  

^a Equipe Rech Oxydation Formulation   (France)

^b UNIVERSITY OF STUTTGART   (Germany)

^c UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001089188     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1999.tb08247.x     Document Type: Conference Paper

References (40)

1. Frimer, A. A. (1985) Singlet Oxygen. CRC Press, Boca Raton, FL.
2. Wasserman, H. H. and R. W. Murray (1979) Singlet Oxygen, Vol. 40. Academic Press, New York.
3. Ranby, B. and J. F. Rabek (1975) Singlet Oxygen. J. Wiley and Sons, New York.
4. Prein, M. and W. Adam (1996) The Shenck Ene Reaction: diastereoselective oxyfunctionalization with singlet oxygen in synthetic applications. Angew. Chem. Int. Ed. Engl. 35, 477-494.
5. Aubry, J. M. (1985) A search for singlet oxygen in the decomposition of hydrogen peroxide by mineral compounds in aqueous solutions. J. Am. Chem. Soc. 107, 5844-5849.
6. Murray, R. W. and M. L. Kaplan (1969) Singlet oxygen sources in ozone chemistry. Chemical oxygenations using the adducts between phosphite esters and ozone. J. Am. Chem. Soc. 91, 5358-5364.
7. Wasserman, H. H. and J. R. Scheffer (1967) Singlet oxygen reactions from photoperoxides. J. Am. Chem. Soc. 89, 3073-3075.
8. 95Mo NMR and kinetic studies of peroxomolybdic intermediates involved in the course of the catalytic disproportionation of hydrogen peroxide by molybdate ions. Inorg. Chem. 34, 4950-4957.
9. Aubry, J. M. and B. Cazin (1988) Chemical sources of singlet oxygen. 2. Quantitative generation of singlet oxygen from hydrogen peroxide disproportionation catalyzed by molybdate ions. Inorg. Chem. 27, 2013-2014.
10. 2-: competition between epoxidation and peroxidation. J. Mol. Catal. A Chem. 117, 439-447.
11. Aubry, J. M., B. Cazin and F. Duprat (1989) Chemical sources of singlet oxygen. 3. Peroxidation of water-soluble singlet oxygen carriers with the hydrogen peroxide molybdate system. J. Org. Chem. 54, 726-728.
12. Aubry, J. M. and S. Bouttemy (1997) Preparative oxidation of organic compounds in microemulsions with the chemical source of molecular singlet oxygen, sodium molybdate/hydrogen peroxide. J. Am. Chem. Soc. 119, 5286-5294.
13. Linker, T. and L. Fröhlich (1994) Regio- and diastereoselective photooxygenation of chiral 2,5-cyclohexadiene-1-carboxylic acids. Angew. Chem. Int. Ed. Engl. 33, 1971-1972.
14. Van Bekkum, H., C. B. van den Bosch, G. van Minnen-Pathuis, J. C. de Mos and A. M. van Wijk (1971) Reduction of alkyl-substituted benzoic acid with lithium in liquid ammonia. Synthesis of 1-alkyl-2,5-cyclohexadiene-1-carboxylic acids. Recl. Trav. Chim. Pays-Bas 90, 137-149.
15. Acheson, R. M. and R. F. Flowerday (1974) Aromatization of cyclohexadienes through methoxycarbonyl migration or alkyl elimination. J. Chem. Soc., Perkin Trans. 1, pp. 2339-2342.
16. Mah, T., H. M. Sirat and E. J. Thomas (1979) Stereoselectivity of epoxidation of substituted cyclohexa-1,4-dienes: influence of an allylic methoxycarbonyl. J. Chem. Soc., Perkin Trans. 1, pp. 2255-2260.
17. Wilkinson, F., W. P. Helman and A. B. Ross (1996) Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. J. Phys. Chem. Ref. Data 24, 663-1021.
18. Gormann, A. A. and M. A. J. Rodgers (1989) Singlet oxygen. Handbook of Organic Photochemistry, Vol. II (Edited by J. C. Scaiano), pp. 229-247. CRC Press, Boca Raton, FL.
19. Gollnick, K. and H. J. Kuhn (1979) Ene reactions with singlet oxygen. Singlet Oxygen, pp. 287-421. Academic Press, New York.
20. g) in aqueous solution by specific chemical trapping with sodium 1,3-Cyclohxadiene-1,4-Diethanoate. J. Photochem. Photobiol. B Biol. 39, 146-155.
21. Rabideau, P. W. (1989) The Conformational Analysis of Cyclohexenes, Cyclohexadienes, and Related Hydroaromatic Compounds. VCH, Weinheim.
22. Yamagushi, K., S. Yabushito, T. Fueno and K. N. Houk (1981) Mechanism of photooxygenation reactions. Computational evidence against the diradical mechanism of singlet oxygen reactions. J. Am. Chem. Soc. 103, 5043-5046.
23. Davies, A. G. and C. H. Schiesser (1991) A PM3 study of the reactions of propene with singlet oxygen and other enophiiles. Tetrahedron 47, 1707-1726.
24. 5 symmetries. J. Am. Chem. Soc. 105, 5263-5269.
25. Hurst, J. R., S. L. Wilson and G. B. Schuster (1985) The ene reaction of singlet oxygen: kinetic and product evidence in support of a perepoxide intermediate. Tetrahedron 41, 2191-2197.
26. Orfanopoulos, M., I. Smonou and C. S. Foote (1990) Intermediates in the ene reactions of singlet oxygen and N-Phenyl-1,2,4-triazoline-3,5-dione with olefins. J. Am. Chem. Soc. 112, 3607-3614.
27. Frimer, A. A. (1979) The reaction of singlet oxygen with olefins: the question of mechanism. Chem. Rev. 79, 359-387.
28. g) reactivity toward enol ethers: reactivity parameters typical of rapid reversible exciplex formation. J. Am. Chem. Soc. 104, 7098-7104.
29. Turro, N. J. (1985) The role of intersystem crossing steps in singlet oxygen chemistry and photooxidations. Tetrahedron, 41, 2089-2098.
30. Yamagushi, K., Y. Ikeda and T. Fuero (1985) Charge-transfer interactions, exciplex formations and ionic dissociations in singlet oxygen reactions. Tetrahedron 41, 2099-2107.
31. g), with both physical and chemical quenchers: variable-temperature, time resolved infrared luminescence studies. J. Am. Chem. Soc. 110, 8053-8059.
32. Orfanopoulos, M., M. J. Grdina and L. M. Stephenson (1979) Site specificity in the singlet oxygen-trisubstituted olefin reaction. J. Am. Chem. Soc. 101, 275-276.
33. 2 with α,β-unsaturated carboxylic acids. Angew Chem. 97, 1071-1072.
34. Orfanopoulos, M. and C. S. Foote (1985) Regioselective reaction of singlet oxygen with α,β-unsaturated esters. Tetrahedron Lett. 26, 5991-5994.
35. Adam, W. and A. Griesbeck (1986) Regioselective synthesis of 2-(hydroperoxy)-2-methylene butanoic acid derivitives via photooxygenation of tiglic acid derivatives. Synthesis, pp. 1050-1052.
36. Orfanopoulos, M. and M. Stratakis (1991) Solvent effects on the side selectivity of singlet oxygen with α,β-unsaturated esters. New evidence for a perepoxide intermediate. Tetrahedron Lett. 32, 7321-7324.
37. Orfanopoulos, M., M. Stratakis and Y. Elemes (1989) Regioselective reaction of singlet oxygen with cis-alkenes. Tetrahedron Lett. 30, 4875-4878.
38. Stratakis, M. and M. Orfanopoulos (1993) Regioselective formation of cyclic and allyclic hydroperoxides. Synth. Commun. 23, 425-430.
39. 2 to 1-Methylcycloalkenes. Correlation with ground-state geometry. J. Am. Chem. Soc. 102, 1738-40.
40. Linker, T. and L. Fröhlich (1995) Substituent effects in the highly regioselective and diastereoselective ene reaction of singlet oxygen with chiral cyclohexadienes. J. Am. Chem. Soc. 117, 2694-2697.