Experimental and Theoretical Study of [2σ + 2σ + 2π]–Cycloaddition of Quadricyclane and Ethylenes Containing Three Silyl-Groups View Full Text


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Article Info

DATE

2015-04

AUTHORS

Maxim Bermeshev, Pavel Chapala, Valentin Lakhtin, Alexander Genaev, Marina Filatova, Alexander Peregudov, Kamil Utegenov, Nikolai Ustynyuk, Eugene Finkelshtein

ABSTRACT

The reaction of [2σ + 2σ + 2π]-cycloaddition of quadricyclane with olefins is an attractive way for regio- and sterospecific synthesis of norbornene derivatives (exo-tricyclononenes) with desired substituents. The presence of Cl3Si-containing groups in such compounds permits different monomer modifications for the development of new materials. Herein, for the first time the theoretical and experimental study of the behavior of different ethylenes containing three silyl-groups in the reaction of [2σ + 2σ + 2π]-cycloaddition with quadricyclane was systematically performed. Based on the data obtained for this reaction the activity scale of the ethylene derivatives was established, and the explanations for an ethylene activity were suggested. As a result, a new family of Si-containing tricyclononenes was successfully synthesized. As an example of a possible modification, the methylation of the sterically hindered cycloadducts was investigated and the conditions for full methylation were found. Considering that gas permeability of polymers increases with the increase of a number of the side Me3Si-groups, the compounds are interesting monomers for synthesis of membrane polymers possessing high gas permeability values. More... »

PAGES

117-126

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s12633-014-9263-6

DOI

http://dx.doi.org/10.1007/s12633-014-9263-6

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1034943810


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