Journal of the Chemical Society. Perkin transactions I p. 319 - 325 (1996)
Update date:2022-07-29
Topics:
Takahashi, Yasutake
Ohaku, Hitoshi
Morishima, Shin-Ichi
Suzuki, Takanori
Ikeda, Hiroshi
Miyashi, Tsutomu
The photochemical reactivities of 1,1-diarylspiropentanes 1a-c have been investigated under various photolysis conditions. Upon direct photolysis or acetone-sensitized photolysis, 1 underwent skeletal rearrangement to afford methylidenecyclobutanes 2, 3 and 4. A mechanism involving diradical intermediates has been proposed. Also studied were the photochemical and thermal reactions of the electron donor-acceptor (EDA) complexes of 1 with tetracyanoethylene (TCNE). Photoirradiation of the charge-transfer (CT) absorption bands of the EDA complexes resulted in the skeletal rearrangement of 1 to 2 and 3, with concomitant formation of TCNE adducts 11b,c and 12a-c. The X-ray structure of 11c is reported. A mechanism involving ion radical pairs [1?+, TCNE?-] is proposed for the photoreaction. In contrast, no skeletal rearrangement was observed in the thermal reaction of the EDA complexes although i1b and 11c were produced.
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