• Journal of the Korean Chemical Society
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• v.40 no.7
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• pp.483-491
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• 1996

Dieis-Alder reaction between cyclopentadiene and 5-membered ring compounds which have exo-cyclic double bond has been studied using the PM3 method. Transition states do not show large geometrical change with the variation of dienophiles. Two isomers are possible due to the rotation of the exo-cyclic double bond of a dienophile. The reactivity for the formation of different products are explained using the FMO energy gap. The exo and endo selectivity of the reaction has been also studied from the correlation between the deformation energy and the activation barrier. Minimum energy reaction path is discussed using the Curtin-Hammett principle.

• Archives of Pharmacal Research
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• v.21 no.1
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• pp.73-75
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• 1998

In summary, six 4-substituted-1-azzanthraquinones were designed and synthesized using hetero Diels-Alder reaction as a key step. Although a great number of reaction conditions for benzylic bromination were examined, this step need to be improved for the efficient synthesis of the related analogues. 4-Bromomethyl-1-azzanthraquinone 6 may have potential for the treatment of tumors resistant to the doxorubicin. The compounds 9 and 10 containing the latent alkylating functionality may need further in depth biological evaluation. Work is in progress to design, synthesize, and evaluate additional compounds in this and related systems.

• Bulletin of the Korean Chemical Society
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• v.23 no.6
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• pp.829-837
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• 2002

Recently it was reported that cycloaddition of 6,6-disubstituted cyclohexa-2,4-dienone, 1 with cyclopentadiene gave solely the adduct of type 1.while its reaction with 1,3-cyclohexadiene gave both Ⅱ and Ⅲ. Semiempirical MO calculations were done to elucidate the origin of the selectivity difference between the two dienes. Cycloaddition of 1 with cyclopentadiene is controlled thermodynamically to give only 1-diene adduct by ΔGvalues of 10.6-20.3 kcal/mol, while its reaction with 1,3-cyclohexadiene does not show 1-diene/1-dienophile selectivity due to similar stabilities of the two adducts. Thermodynamic parameters also show that 두애 adducts are more fabourably fromed in the cycloadditions of 1 with both cyclopentadiene and 1,3-cyclohexadiene, which coincides with experimental observations. Cope rearrangements of endo adducts are another avenue to convert between 1-diene and 1-dienophile.

• Bulletin of the Korean Chemical Society
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• v.8 no.5
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• pp.376-380
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• 1987

The cyclobutane forming photocycloaddition reaction of 5(E)-styryl-1,3-dimethyluracil with some olefins occurs on the 5,6-double bond of uracil ring rather than the expected central double bond via an intermediate, probably the photochemical Diels-Alder type adduct. This intermediate formed on short term irradiation of 5(E)-styryl-1,3-dimethyluracil and 2,3-dimethyl-2-butene solution is converted into the $C_4$-cycloadduct on the prolonged irradiation. Quantum yield of the intermediate formation is not linear with the concentration of 2,3-dimethyl-2-butene probably due to the secondary reaction accompanied with the complex reaction kinetics. The intermediate is formed from the lowest excited singlet state.

• Proceedings of the Korean Society of Dyers and Finishers Conference
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• 2001.04a
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• pp.167-172
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• 2001

• Bulletin of the Korean Chemical Society
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• v.12 no.2
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• pp.125-126
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• 1991

• Bulletin of the Korean Chemical Society
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• v.22 no.6
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• pp.543-544
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• 2001

• Bulletin of the Korean Chemical Society
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• v.11 no.3
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• pp.178-179
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• 1990

• Bulletin of the Korean Chemical Society
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• v.10 no.2
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• pp.129-132
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• 1989

Reactions of thebaine with phenylsulfonylpropadiene in various solvents were investigated. It was found that Diels-Alder reaction adduct was obtained in nonpolar solvent, while addition reaction adduct was obtained in polar solvent. Transformations of these two products were also carried out.

• Bulletin of the Korean Chemical Society
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• v.29 no.10
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• pp.1993-1997
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• 2008

In the present work, Diels-Alder reaction of cyclopentadiene with ethylacrylate has been carried out by using two types of mesoporous solid acid catalysts (Al-MCM-41, Al-MCM-48) with different pore structures. The specific topology of Al-MCM-48 (cubic Ia3d structure composed of two independent 3-D channel systems) exhibit higher activity and stereo-control than those of Al-MCM-41 (hexagonal packing of 1-D channels). The physical properties of Al-MCM-48 catalyst, such as high accessibility of reactants to the acid sites, spatial confinement in the nanoscopic reactors, and 3-D channel network structure that are effective adsorption and diffusion of reactants, play a crucial role in the present study.