Photoreaction of a 2,11-diaza[3.3]paracyclophane derivative: formation of octahedrane by photochemical dimerization of benzene.
Upon photoirradiation at 300 nm, the title diazaparacyclophane (R = COCF3) provided an octahedrane by the photodimerization of its benzene chromophores. This is the first photochemical formation of octahedrane, namely, via the dimerization of benzene. No octahedrane formation was observed for the photolysis of corresponding carbon-bridged paracyclophane. Thus the nitrogen bridges play an important role in the excited state to afford the octahedrane.
Okamoto
Hideki
H
Division of Chemistry and Biochemistry, The Graduate School of Natural Science and Technology, Okayama University, Tsushima-Naka 3-1-1, Okayama 700-8530, Japan. hokamoto@cc.okayama-u.ac.jp
Satake
Kyosuke
K
Ishida
Hiroyuki
H
Kimura
Masaru
M
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D001554:Benzene / Q000737:chemistry* / Q000528:radiation effects*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D018360:Crystallography, X-Ray; D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010777:Photochemistry; D012680:Sensitivity and Specificity; D014466:Ultraviolet Rays
C516927:2,11-diaza(3.3)paracyclophane; D001372:Aza Compounds; D001952:Bridged-Ring Compounds; C516928:octahedrane; D001554:Benzene