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A Diels–Alder approach to trans-trisbicyclo[2.2.1]heptabenzene derivative

✍ Scribed by Zhong-Qiang Gao; Jun-Fa Wei; Xian-Ying Shi; Jun Yu


Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
273 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis


A new route to the synthesis of a trans-tris(bicyclo[2.2.1]hexeno)benzene derivative, using Diels-Alder reaction as critical step, was investigated. The compound with six methoxycarbonyl groups was successfully synthesized in good yield without any organometallic reagents. Some useful by-products from dimethyl but-2-ynedioate were also isolated from the last step. Perhaps due to stereo-hindrance or electrostatic repulsion in the cis-isomer, trans-isomer was found to be the only isomer in the crystal and its structure was proved by X-ray diffraction.


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