Cage Polycyclic Hydrocarbons Based on Adducts of Norbornadiene-2,5 and Anthracene Derivatives


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Abstract

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.

About the authors

S. V. Shorunov

Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Email: bmv@ips.ac.ru
Russian Federation, Moscow, 119071

M. A. Rudakova

Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences; Mendeleev University of Chemical Technology of Russia

Email: bmv@ips.ac.ru
Russian Federation, Moscow, 119071; Moscow, 119999

M. E. Fil’kina

Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Email: bmv@ips.ac.ru
Russian Federation, Moscow, 119071

Yu. V. Nelyubina

Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: bmv@ips.ac.ru
Russian Federation, Moscow, 121609

M. V. Bermeshev

Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences; Mendeleev University of Chemical Technology of Russia

Author for correspondence.
Email: bmv@ips.ac.ru
Russian Federation, Moscow, 119071; Moscow, 119999

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