Cage Polycyclic Hydrocarbons Based on Adducts of Norbornadiene-2,5 and Anthracene Derivatives
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Double adducts of norbornadiene-2,5 and anthracene derivatives have been synthesized using the Diels–Alder reaction. The possibility of selective preparation of both symmetrical and unsymmetrical adducts depending on the reaction conditions has been shown. For these cycloadducts exclusively consisting of carbon and hydrogen, an unusual and interesting feature has been revealed, namely, the signals of the protons of the bridge methylene groups in the 1H NMR spectra have chemical shifts in the negative region. In this work, double adducts of anthracene derivatives and norbornadiene (2,5-(bicyclo-[2.2.1]-hepta-2,5-diene)) have been synthesized and their structure investigated. The synthesized compounds possess a rigid, branched, and bulky structure suitable for the fabrication of composite membrane materials.
Keywords:norbornadiene anthracene cycloaddition cage hydrocarbons NMR spectroscopy
The authors are grateful to the “Biospectrotomography” shared-use center of the Moscow State University for the use of an NMR spectrometer. X-ray diffraction studies were supported by the Ministry of Science and Higher Education of the Russian Federation with the use of the scientific equipment of the Center for Molecular Structure Investigation of the Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences.
This work was performed as part of a state task for the Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences.
CONFLICT OF INTEREST
The authors declare no conflict of interest to be disclosed in this work.