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Structure and Reactivity of Bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboxylic (endic) Acid Hydrazide

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Abstract

Establishing of the structure of hydrazinolysis product obtained from bicyclo[2.2.1]hept-2-ene-endo-5, endo-6-dicarboxylic (endic) acid was performed by preparation of the compound under alternative conditions followed by comparison of the characteristics and spectral parameters of the resulting substances, and also by quantum-chemical calculations by the density functional method of the chemical shifts in 1H and 13C NMR spectra of different reaction products. The X-ray diffraction analysis of the hydrazide was also carried out. The compound obtained was assigned a structure of N-aminobicyclo[2.2.1] hept-2-ene-endo-5,endo-6-dicarboximide. The products were prepared by its reactions with arylsulfonyl chlorides, benzoyl chlorides, m-tolyl and p-toluene-sulfonyl isocyanates, phenyl isothiocyanate, with o-nitrobenzaldehyde, and oxiranes (1,2-epoxycyclohexane and 2,3-epoxypropylcarbazole). The aromatic sulfonamides, carboxamides, and ureas were epoxidized by performic acid obtained in situ from the formic acid and hydrogen peroxide. Products of [3+2]-cycloaddition of aryl azides to the strained double bond in the N-aminobicyclo[2.2.1] hept-2-ene-endo-5,endo-6-dicarboximide and its derivatives. The structures of compounds obtained were confirmed by their IR, 1H and 13C NMR spectra.

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Authors and Affiliations

  1. Dnepropetrovsk National University, Dnepropetrovsk, 49050, Ukraine

    L.I. Kas'yan, I.N. Tarabara & Ya.S. Bondarenko

  2. Institute of Single Crystals, National Academy of Sciences of Ukraine, Khar'kov, Ukraine

    S.V. Shishkina, O.V. Shishkin & V.I. Musatov

Authors
  1. L.I. Kas'yan
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  2. I.N. Tarabara
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  3. Ya.S. Bondarenko
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  4. S.V. Shishkina
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  5. O.V. Shishkin
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  6. V.I. Musatov
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__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 8, 2005, pp. 1145–1154.

Original Russian Text Copyright © 2005 by Kas'yan, Tarabara, Bondarenko, Shishkina, Shishkin, Musatov.

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Kas'yan, L., Tarabara, I., Bondarenko, Y. et al. Structure and Reactivity of Bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboxylic (endic) Acid Hydrazide. Russ J Org Chem 41, 1122–1131 (2005). https://doi.org/10.1007/s11178-005-0305-9

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  • DOI: https://doi.org/10.1007/s11178-005-0305-9

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