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LASER FLASH PHOTOLYSIS STUDY ON THE PHOTOCYCLIZATION OF N-(O-HALOBENZYL) IMIDAZOLE

Park, Yong-Tae    (Department of Chemistru, Kyungpook National University   ); Hwang, Young-Sun    (Department of Chemistru, Kyungpook National University   ); Song, Woong Song    (Korea Research Institute of Standards and Science   ); Kim, Dongho    (Korea Research Institute of Standards and Science  );
  • 초록

    In connection with our interest on the photochemical properties of heteroaryl halides, which are currently the subject of heterocyclic ring formation and haloarene degradation, we have studied the photochemistry of the haloarene linked to N-heteroarene compounds. Imidazo[5,1-a]isoindole was synthesized from N-(ochlorobenzyl)imidazole or N-(o-bromobenzyl) imidazole in acidic aqueous solution or acetonitrile via the intramolgcular photocyclization (Table 1). This type of reaction provides the synthetic methods for 5- and 6-membered polyheteroatomic heterocyclic ring compounds. However, the reaction mechanism for the intramolecular photocyclization of haloarene tethered heteroarenes has not yet been established. Grimshaw et al. suggested a mechanism for homolyric carbonhalogen bond fission assisted by radical complexation to explain their results in the photocyclization of 5-(2-chlorophenyl)-1,3-diphenylpyrazole. They also reported the detection of acyclohexadienyl intermediate involved in the above reaction. Park et al. reported several transient 'intermediates involved in the laser flash photolysis of N-(o-halobenzyl) pyridinium and N-benzyl-2-halopyridinium salts. Thus we performed the laser flash photolysis study on the photocyclization reaction of N-(o-chlorobenzyl) imidazole to identify the intermediate species involved in the reaction. Here, we report on the preliminary results in the photocyclization reaction of N-(o-halobenzyl)imidazole through the detection of reaction intermediates.


  • 참고문헌 (6)

    1. Flash Photolysis Observation of Aryl, 2,3-Dihydrocyclohexadienyl, and Halogen Anion Radicals in Aqueous Solution: Photohomolytic Radical Cyclization of Aryl Halides , Park, Y.-T.;N. W. Song;Y.-H. Kim;C.-G. Hwang;S. K. Kim;D. Kim , J. Am. Chem. Soc. / v.,pp.,
    2. Spin Trapping , Janzen, E. G. , Acc. Chem. Res. / v.4,pp.31-40,
    3. Photocylization of 1,3-Diphenyl-5-(2-halogenophenyl) pyrazoles: a Mechanism of Homolytic Carbon-Halogen Bond Fission Assisted by Radical Complexation , Grimshaw, J.;A. Prasanna de Silva , J. Chem. Soc. / v.,pp.193-194,
    4. An Intermediate in the Aryl Halide Photocyclization Process Detected by Flash Photolysis , Grimshaw, J.;J. Trocha-Grimshaw , J. Chem. Soc., Chem. Commun. / v.,pp.744-745,
    5. Transient Absorption Spectra from the Photolysis of N-(2-Bromophenyl)alkyl-pyridinium Bromides: Detection of Phenyl, 2,3-dihydropyridinium, and Bromine Anion Radicals , Park, Y.-T.;Y.-H. Kim;S. K. Kim;N. W. Song , Bull. Kor. Chem. Soc. / v.15,pp.607-608,
         
    6. Synthesis of 5H-Imidazo[5,1-a]isoindole: Photocyclization of N,N-Bis(o-chlorobenzyl)imidazolium chloride and N-(o-chlorobenzyl)imidazole , Byun, Y.-S.;C.-H. Jung;Y.-T. Park , J. Heterocyclic Chem. / v.32,pp.1835-1837,

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