[2.2]-パラシクロファン

解説C16H16(208.30)．[2.2]-パラシクロファンは，2個のベンゼン環のパラ位を2個のエチレン鎖で結んだ，パラシクロファンの一種．1,4-ビス[メルカプトメチル]ベンゾールを酸化的に二量化した2,11-ジチア[3.3]パラシクロファンを，亜リン酸エチルの存在下で光還元により脱硫して合成する．白色の針状晶．融点285～287 ℃．二つのベンゼン環が平行状態でひずんで結合されているので，物性に興味がもたれている．森北出版「化学辞典（第2版）

説明[2.2]Paracyclophane is used as an intermediate in organic synthesis or as a reagent in chemical reactions. It serves as the structural backbone of 4-toluenesulfinyl [2.2]p-dicyclohexane and can be used in the synthesis of various mono- and disubstituted [2.2]p-dicyclohexane derivatives. It can also be used for the preparation of metal complexes, and the interaction of the Ag+ cation with the cation -π of [2.2]paracyclophane can be used to synthesise Ag+ - [2.2]paracyclophane complexes using the Ag+ cation. The complex is formed by binding the cation Ag+ to three carbon atoms on a benzene ring of the [2.2]paracyclophane ligand using a cation-π interaction[1].

使用2,2]-Paracyclophane is the raw material for the synthesis of parylene which is widely used in microelectronic integrated circuit.

純化方法Purify it by recrystallisation from AcOH. 1H-NMR : 1.62 (Ar-H) and -1.71 (CH2) [Waugh & Fessenden J Am Chem Soc 79 846 1957, IR and UV: Cram et al. J Am Chem Soc 76 6132 1954, Cram & Steinberg J Am Chem Soc 73 5691 1951. It complexes with unsaturated compounds: Cram & Bauer J Am Chem Soc 81 5971 1959, Syntheses: Brink Synthesis 807 1975, Givens et al. J Org Chem 44 16087 1979, Kaplan et al. Tetrahedron Lett 3665 1976]. [Beilstein 5 IV 2223.]