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Volumn 72, Issue 26, 2007, Pages 10075-10080

New insight into the reaction of singlet oxygen with sulfur-containing cyclic alkenes: Dye-sensitized photooxygenation of 5,6-dihydro-1,4-dithiins

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION; MOLECULAR INTERACTIONS; OXYGEN; REACTION KINETICS; STEREOSELECTIVITY; SULFUR;

EID: 37549044719     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701983v     Document Type: Article
Times cited : (11)

References (37)
  • 1
    • 0000412621 scopus 로고    scopus 로고
    • For some reviews: a
    • For some reviews: (a) Clennan, E. L. Sulfur Rep. 1996, 19, 171.
    • (1996) Sulfur Rep , vol.19 , pp. 171
    • Clennan, E.L.1
  • 2
    • 0002393586 scopus 로고
    • Baumstark, A. L, Ed, JAI Press: Greenwich, CT
    • (b) Jensen, F. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 4, pp 1-48.
    • (1995) Advances in Oxygenated Processes , vol.4 , pp. 1-48
    • Jensen, F.1
  • 3
    • 0002624208 scopus 로고
    • Frimer, A. A, Ed, CRC Press: Boca Raton, FL
    • (c) Ando, W.; Takata, T. In Singlet Oxygen; Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; Vol. III, part 2.
    • (1985) Singlet Oxygen , vol.3 , Issue.PART 2
    • Ando, W.1    Takata, T.2
  • 7
    • 0004164999 scopus 로고
    • Ando, W, Ed, J. Wiley and Sons: New York
    • (a) Akasaka, T.; Ando, W. In Organic Peroxides; Ando, W., Ed.; J. Wiley and Sons: New York, 1992; p 599.
    • (1992) Organic Peroxides , pp. 599
    • Akasaka, T.1    Ando, W.2
  • 14
    • 37549051269 scopus 로고    scopus 로고
    • The use of a dye, visible light, and molecular oxygen is one of the most common and efficient procedures to produce singlet oxygen. Foote, C. S.; Clennan, E. L. In Active Oxygen in Chemistry; Foote, C. S., Valentine, J. S., Greenberg, A., Liebman, J. F., Eds.; Chapman and Hall: London, 1995; p 105.
    • The use of a dye, visible light, and molecular oxygen is one of the most common and efficient procedures to produce singlet oxygen. Foote, C. S.; Clennan, E. L. In Active Oxygen in Chemistry; Foote, C. S., Valentine, J. S., Greenberg, A., Liebman, J. F., Eds.; Chapman and Hall: London, 1995; p 105.
  • 15
    • 0000337623 scopus 로고    scopus 로고
    • A symmetrically substituted dithiin (2,3-diphenyl derivative) was previously photooxygenated giving the corresponding dicarbonyl compound and benzyl: Handley, R. S.; Stern, A. J.; Schaap, A. P. Tetrahedron Lett. 1985, 26, 3183.
    • A symmetrically substituted dithiin (2,3-diphenyl derivative) was previously photooxygenated giving the corresponding dicarbonyl compound and benzyl: Handley, R. S.; Stern, A. J.; Schaap, A. P. Tetrahedron Lett. 1985, 26, 3183.
  • 19
    • 37549020013 scopus 로고    scopus 로고
    • The lower stability of electron-withdrawing substituted dioxetanes than that of alkyl- or aryl-substituted analogues has already been observed in the oxathiin systems.7a
    • 7a
  • 20
    • 0026101787 scopus 로고    scopus 로고
    • Rearrangements of labile epoxides to carbonyl compounds are well-documented. See, for example: (a) Adam, W.; Hadjiarapoglou, L.; Wang, X. Tetrahedron Lett. 1991, 32, 1295.
    • Rearrangements of labile epoxides to carbonyl compounds are well-documented. See, for example: (a) Adam, W.; Hadjiarapoglou, L.; Wang, X. Tetrahedron Lett. 1991, 32, 1295.
  • 23
    • 37549044222 scopus 로고    scopus 로고
    • 8 In both cases, dithiins were recovered unchanged even after prolonged irradiation times.
    • 8 In both cases, dithiins were recovered unchanged even after prolonged irradiation times.
  • 26
    • 2142751209 scopus 로고
    • Wasserman, H. H, Murray, R. W, Eds, Academic Press: New York
    • Schaap, A. P.; Zaklika, K. A. In Singlet Oxygen; Wasserman, H. H., Murray, R. W., Eds.; Academic Press: New York, 1979; p 234.
    • (1979) Singlet Oxygen , pp. 234
    • Schaap, A.P.1    Zaklika, K.A.2
  • 27
    • 37549005534 scopus 로고    scopus 로고
    • It is interesting to note that the oxidation of 1b with MCPBA showed the same chemoselectivity affording sulfoxide 4b: unpublished results from G. Palumbo and A. Guaragna.
    • It is interesting to note that the oxidation of 1b with MCPBA showed the same chemoselectivity affording sulfoxide 4b: unpublished results from G. Palumbo and A. Guaragna.
  • 28
    • 0000369657 scopus 로고    scopus 로고
    • Trapping of persulfoxides by alkenes with formation of epoxides is reported: Akasaka, T.; Sakurai, A.; Ando, W. J. Am. Chem. Soc. 1991, 113, 2696.
    • Trapping of persulfoxides by alkenes with formation of epoxides is reported: Akasaka, T.; Sakurai, A.; Ando, W. J. Am. Chem. Soc. 1991, 113, 2696.
  • 29
    • 37549042761 scopus 로고    scopus 로고
    • In the oxygenation of oxathiins, the related epoxide rearranges via both O-migration and SO-migration, and the latter is the relevant mode.7 In the dithiin series, sulphur migration overcomes completely the sulfoxide-migration
    • 7 In the dithiin series, sulphur migration overcomes completely the sulfoxide-migration.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.