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PHOTOCHEMICAL FORMATION OF ISOMERIC QUINONE METHIDES FROM o-QUINONES AND ONE-WAY ISOMERIZATION

Kim, Ae-Rhan    (Department of Chemistry, Chonbuk National University  );
  • 초록

    Irradiation (300 nm) of 1, 2-benzoquinones 1 and diphenylacetylene 2 in dichloromethane yielded two isomeric quinone methides, 6 and 7. The same types of quinone methides, 9 and 10 (or 12 and 13) were obtained from the photocycloadditions of 9, 10-phenanthrenequinone 8 (or acenaphthenequinone 11) to diphenylacetylene 2. One-way photoisomerizations were observed between each isomeric adducts, (6, 7), (9, 10) and (12, 13).


  • 참고문헌 (7)

    1. Photoaddition reactions of 9,10-phenanthrenequinone and acenaphthenequinone to conjugated molecules , Kim, S. S.;D. Y. Yoo;A. R. Kim;S-K. Park;S. C. Shim , Bull. Korean Chem. Soc. / v.16,pp.983-984,
    2. Maruyama, K.;A. Osuka;S. Patai(ed.);Z. Rappoport(ed.) , The Chemistry of the Quinonoid Compounds, Part 1 / v.,pp.759-874,
    3. Photoaddition reactions of ο-benzoquinones to 1,4-diphenylbut-1-en-3-yne: formation of phenanthrenes and dihydrodioxins , Kim, S. S.;Y. J. Mah;A. R. Kim;D. J. Yoo;S. C. Shim , Bull. Korean Chem. Soc. / v.17,pp.577-579,
    4. Formation and oxidation of 1:1 adducts of tetrahalo-1,2-benzoquinones and 1,3-diene , Kim, S. S.;Y. H. Yu;S. C. Shim;I. H. Cho , Tetrahedron Lett. / v.35,pp.9039-9042,
    5. Photoaddition of phenanthraquinone to alkyl-substituted alkoxyacetylenes. Formation of 1,3-dioxoles , Bos, H. J. T.;H. Polman;P. F. E. van Montfort , J. Chem. Soc., Chem. Commun. / v.,pp.188,
    6. Laird, T.;J. F. Stoddart(ed.) , Comprehensive Organic Chemistry / v.1,pp.1213,
    7. Photochemical and thermal cycloaddition of cis-stilbene and tolan (diphenylacetylene) to tetrachloro-ο-benzoquinone, photodecarbonylation of an alpha-diketone , Bryce-Smith, D.;A. Gilbert , Chem. Commun. / v.24,pp.1702-1703,
  • 이 논문을 인용한 문헌 (1)

    1. 1998. "" Journal of photoscience : an international journal officail organ of the korean society of photoscience, 5(4): 143~148     

 저자의 다른 논문

  • Kim, Aeran (23)

    1. 1989 "Photoaddition Reactions of Alkynes to Quinonoid Compounds" Bulletin of the Korean Chemical Society 10 (1): 57~60    
    2. 1989 "Photoaddition Reactions of p-Quinones to Conjugated Diyne" Bulletin of the Korean Chemical Society 10 (1): 66~69    
    3. 1999 "Photoaddition Reactions of 1 , 4 Diphenylbut -1-EN-3-YNE to Quinones" Journal of photoscience : an international journal officail organ of the korean society of photoscience 6 (1): 7~12    
    4. 2000 "Photochemical Formation of 3-Methoxycyclohex-2-en-1-ones from 1,3-Cyclohexanedione and 2-Allyl-3-hydroxycyclohex-2-en-1-one in Methanol in the Presence of Quinones" Journal of photoscience : an international journal officail organ of the korean society of photoscience 7 (3): 111~114    
    5. 2004 "Synthesis, Fabrication and Characterization of Photorefractive Composite Utilizing Flexible NLO Chromophores and Crosslinkable Photoconducting Matrix" Journal of photoscience : an international journal officail organ of the korean society of photoscience 11 (3): 101~106    
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    9. 2012 "CONVOLUTION SUM ∑k<N/3σ1(3mk)σ1(2n(N-3k))" Honam mathematical journal = 호남수학학술지 34 (4): 519~531    
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