1,1-Difluoronaphtalene-2(1H)-ones in synthesis of tetraphene derivatives
Ok Ton Dyan1, P. Zaikin1, G. Borodkin1,2 and V. Shubin1
1
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
Siberian Branch of the Russian Academy of Sciences
630090, Russia, Academician Lavrentiev Ave., 9
2
Novosibirsk State University, 630900, Russia, Novosibirsk, Pirogov St., 2
E-mail: dyan_ok@nioch.nsc.ru
Substituted polyaromatic compounds belong to one of the most promising class of compounds
to be used as organic semiconductors [1]. Such compounds may supposedly be synthesized by the
Diels-Alder reaction of substituted naphtalenones with subsequent aromatisation of cycloaddition
adducts.
In this study we synthesized a number of polycyclic compounds by using 6-X-1,1difluoronaphtalene-2(1H)-ones in [4+2]-cycloaddition reaction with 1,3-diphenylisobenzofuran and
α,α,α’,α’-tetrabromo-o-xylene.
Dependence of conversion on the reaction conditions was investigated along with dependence
of stereoselectivity in case of cycloaddition with 1,3-diphenylisobenzofuran.
This work was supported by Division of Chemistry and Material Sciences of the Russian Academy of
Sciences (project 5.1.4)
References:
[1] Yamashita, Y., Sci. Technol. Adv. Mater.. 2009, 10 (2), 024313