Photoisomerization of 1-triphenylmethylcyclopentadiene. Di-π-methane rearrangement to 5,6,6-triphenylbicyclo[3.1.0]hex-2-ene
Triphenylmethylcyclopentadiene exists as a mixture of isomers, the minor and major components of which are shown to be 1-triphenylmethylcyclopentadiene (1) and 2-triphenylmethyl-cyclopentadiene (2), respectively.Direct irradiation of a mixture of 1 and 2 led to formation of 5,6,6,-triphenylbicyclo[3.1.0]hex-2-ene (3) via rearrangement of 1. Acetophenone-sensitized irradiation of the same mixture gave 3 as well as a two component mixture of photodimers of 1 and/or 2. Results are interpreted in terms of the di-π-methane rearrangement mechanism.
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