159591-87-4Relevant academic research and scientific papers
Catalytic Hydrogenation of Paracyclophane. Unsaturated Intermediates
Lin, Shaw-Tao,Wharry, Donald L.,Yates, Robert L.,Garti, Nissim,Pranata, Julianto,et al.
, p. 7056 - 7060 (1994)
The catalytic hydrogenation of paracyclophane (1) was repeated to determine whether the claim that 1 yields an octahydroparacyclophane (2) which contains a 1,4-cyclohexadienic structural unit can be substantiated.Decahydroparacyclophane and three isomeric dienes (I-III), as well as perhydroparacyclophane, are isolated.The NMR spectra (1H and 13C) of the dienes are inconsistent with the earlier proposal, and the failure of the dienes to be aromatized by treatment with DDQ indicates that the trisubstituted double bonds reside in different six-membered rings.Computations of conformational energies aid the assignment of structures to the dienes.
