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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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