Description
[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].
Chemical Properties
WHITE TO LIGHT BEIGE CRYSTALS OR CRYSTAL. POWDER
Uses
2,2]-Paracyclophane is the raw material for the synthesis of parylene which is widely used in microelectronic integrated circuit.
Synthesis Reference(s)
The Journal of Organic Chemistry, 46, p. 1043, 1981
DOI: 10.1021/jo00318a047
Flammability and Explosibility
Not classified
Purification Methods
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.]
References
[1] DR. PETR VA?URA; Dr. T U; Prof David Sykora. Interaction of the Silver(I) Cation with [2.2]Paracyclophane: Experimental and Theoretical Study[J]. ChemistrySelect, 2022. DOI:10.1002/slct.202203008.
