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A convenient preparation of octafluoro[2,2]paracyclophane and dodecafluoro[2,2]paracyclophane

✍ Scribed by Shi-zheng Zhu; Yun-yu Mao; Gui-fang Jin; Chao-yue Qin; Qian-li Chu; Chang-ming Hu

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
168 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new and convenient synthesis of octafluoro[2,2]paracyclophane and dodeca-fluoro[2,2]paracyclophane is reported. It is accomplished by treatment of 1,4-bis(halodifluoromethyl)benzene with PbBr 2 /Al in DMF at room temperature via the cyclocoupling of the reactive intermediate a,a,a%a%-tetrafluoro-p-xylylene.

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The [2.1.2.l]paracyclophanedienes 9-11 were prepared in good yields by a McMurry cyclization of the bis(4-acylphen-y1)methanes 5 and 6 and of bis(4-acetylphenyl) ether (?), respectively.