Synthesis of Perfluoro[2.2]paracyclophane

A synthesis of perfluoro[2.2]paracyclophane has been sought
ever since the partially fluorinated octafluoro[2.2]paracyclophane (AF4) was prepared and its chemistry
studied. This compound has now been prepared in 39% yield
from the precursor, 1,4-bis(chlorodifluoromethyl)-2,3,5,6-tetrafluorobenzene by its reaction with Zn when heated in
acetonitrile at 100 °C. Two preparations of the precursor,
first from 1,4-dicyano-2,3,5,6-tetrachlorobenzene and an
improved method beginning from 1,2,4,5-tetrachlorobenzene,
are also described as are key comparisons to our related
synthesis of AF4.

自部分氟化的八氟[2.2]双环戊二烯（AF4）被合成并对其化学性质进行研究以来，对其合成物全氟[2.2]双环戊二烯的制备一直备受关注。目前，该化合物已从前体1,4-双（氯二氟甲基）-2,3,5,6-四氟苯中以39%的产率成功制备，其制备过程是通过在100°C的乙腈中与锌反应实现的。此外，还描述了两种前体的制备方法，一种始于1,4-二氰-2,3,5,6-四氯苯，另一种采用改进的方法，始于1,2,4,5-四氯苯，以及与我们的相关AF4合成的关键比较。