A new synthesis of large polyaromatic hydrocarbons (PAHs) with low Clar sextets is reported (see figure). The synthetic protocol involves starting bis(biaryl)diynes, which undergo initial PtCl2-catalyzed aromatizations, and subsequent 2,3-dichloro-5,6-dicyano benzoquinone (DDQ) oxidation.
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Chen et al. (2011) studied this question.
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