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A matrix isolation study of 2-isopropylidenecyclopentane-1,3-diyl (Berson-type diradical)
Manabu Abe1, Satoshi Kawanami, Araki Masuyama
1Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita565-0871, Osaka, Japan. abe@chem.eng.osaka-u.ac.jp
Abstract:
The photodenitrogenation of diazene 5 in an argon matrix at 10 K permitted the first observation of an IR spectrum of 2-isopropylidenecyclopentane-1,3-diyl 2 (a Berson-type diradical). A comparison of the IR spectrum with a vibrational simulation at the B3LYP/6-31G(d) level of theory revealed that the diradical 2 has a planar structure. The oxygen-trapping reaction of 2 produced regioselectively fused peroxide 6 in an oxygen-doped argon matrix at 10 K. Irradiation of the diradical 2 afforded enyne 8 in an argon matrix at 10 K.
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