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Synfacts 2009(10): 1095-1095  
DOI: 10.1055/s-0029-1217936
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Trisannulation to a Thio-Bridged Triphenylene

Contributor(s): Timothy M. Swager, Jan M. Schnorr
J. Wei*, X. Jia, J. Yu, X. Shi, C. Zhang, Z. Chen
Shaanxi Normal University, Xi’an, P. R. of China
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

Triphenylene (1) based polycyclic aromatic hydrocarbons (PAHs) such as coronene (2), sumanene (3) and trithiosumanene (4) are an interesting class of molecules due to various applications in materials chemistry. The authors describe a new approach to a triphenylene 8 which carries one thio- and two dithio-bridges in its bay regions. It is synthesized by ZrCl4-catalyzed tri­merization of cyclohexanone (5), subsequent bromination to the all-trans isomer 7 and trisannulation followed by aromatization with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ).