222-93-5Relevant articles and documents
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Marsili,A.,Isola,M.
, p. 1037 - 1041 (1967)
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Synthesis of Polycyclic Aromatic Hydrocarbons (PAHs) via a Transient Directing Group
Tang, Ming,Yu, Qinqin,Wang, Ziqi,Zhang, Chen,Sun, Bing,Yi, Ying,Zhang, Fang-Lin
supporting information, p. 7620 - 7623 (2018/12/11)
In this work, an efficient synthetic route was developed to construct PAHs with diverse shape, width, and edge topology. The precursors of PAHs were obtained by using a direct arylation of arenes via a transient ligand-directed C-H functionalization strategy and the cycloaromatization was readily achieved by using a Br?nsted acid catalyst. This novel route provides an opportunity to build up PAHs in a highly efficient manner.
A Rapid, Convergent, and Regioselective Synthesis of Anthracenes
Fitzgerald, John J.,Drysdale, Neville E.,Olofson, R. A.
, p. 7122 - 7126 (2007/10/02)
Anthracenes are obtained in moderate to good yield by the simultaneous treatment of benzocyclobutenols and halobenzenes with LTMP in tetrahydropyran.In the key step of this one-pot process, o-toluoyl anion intermediates from the known ring-opening of benzocyclobutenoxides add to halobenzene derived arynes.Methoxy-substituted benzocyclobutenols which are readily made regiospecifically by known methods also react regiospecifically with the single benzyne generated from either a 2- or 3-haloanisole.For example, the only trimethoxyanthracene isolated (48percent yield) from the reaction of 6-methoxybenzocyclobutenol (8) with 5-chloro-1,3-dimethoxybenzene is the 1,3,8-isomer 20.When 1,2-dihydrocyclobutaphenanthren-1-ol (14) and/or halonaphthalenes are the reactants, benzannulated anthracenes are formed; e.g., tribenzanthracene in 68percent yield from 14 and bromonaphthalene.In another extension, pentaphene (31) was made in one pot from o-dichlorobenzene.
