Formation and structural features of novel cage compounds with a pentacyclo[6.4.0.03,7.04,11.05,10]dodecane skeleton via photolysis of [33](1,3,5)cyclophane

Arene–Alkene Cycloaddition

“…When aromatic rings are forced into close proximity in a very specific orientation, benzenoid aromatic ring can react together and form very intricate polycyclic systems. For example, cyclophanes were photolyzed by Shinmyozu and co-workers, which led to a series of ladderane-type cores (Scheme ). Earlier, Prinzbach and co-workers , had reported related reactions.…”

Synthesis, Electronic Spectra, and Crystal Structural Properties of Fluorinated [33](1,3,5)cyclophanes

“…Despite much effort, hexaprismane and its derivatives have so far eluded synthesis, mainly due to the lack of appropriate synthetic routes and their expected highly strained nature. In our approach to construct the hexaprismane skeleton by irradiating multibridged [3 n ]cyclophanes ( n = 3−6) with completely stacked benzene rings, we have reported that irradiation of [3 3 ](1,3,5)cyclophane ([3 3 ]CP) 1 as well as [3 4 ](1,2,3,5)- and (1,2,4,5)CP's afforded novel polycyclic cage compounds. These may have been formed by protonation of hexaprismane derivatives, followed by rearrangement of the resultant carbocations and trapping of the stable cations by nucleophiles present under the reaction conditions.…”

Photophysical and Photochemical Processes of Excited Singlet and Triplet [3n]Cyclophanes (n = 2–6) Studied by Emission Measurements and Steady-State and Laser Flash Photolyses

“…[3 n ]Cyclophanes (3 n CP; n = 2–6) were prepared according to the literature reported previously. − Xanthone (XT) was recrystallized from ethanol before use. Acetone (Ac) was purified by distillation whereas cyclohexane (CH, Aldrich, Spectroscopic grade), dichloromethane (Dojin, Uvasol), methylcyclohexane (MCH, Dojin, Uvasol), and isopentane (IP, Merck, Spectroscopic grade) were used as supplied.…”