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February 23, 2006Organic Letters108 citations

Hexa-peri-hexabenzocoronenes by Efficient Oxidative Cyclodehydrogenation:  The Role of the Oligophenylene Precursors

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XFXinliang FengJWJishan WuVEV. Enkelmann

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Abstract

reaction: see text Oligophenylene precursors based on 1,3,5-tris-(2'-biphenyl)ylbenzene (4a) and 1,4-bis-(2'-biphenyl)yl-2,5-diphenylbenzene (5a) were prepared and utilized for efficient hexabenzocoronene (HBC) synthesis by cyclodehydrogenations. Parent HBC 6a was efficiently synthesized from the 1,3,5-tris-(2'-biphenyl)ylbenzene precursor, and novel D(3)(h)() symmetrical HBCs were prepared from 1,3,5-tris-(2'-biphenyl)ylbenzenes with various substitution types. For the preparation of a tert-butyl containing HBC 7 with D(2)(h)() symmetry, a two-step cyclodehydrogenation was required because of changes in the spin density distribution.

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Cite This Study

Feng et al. (2006) studied this question.

synapsesocial.com/papers/6a07719dd9167a9c2a586152https://doi.org/10.1021/ol053043z
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