Abstract
Irradiation of(Z)-α, β-diarylacrylonitriles (1) ArCH=C(CN)Ar′ (a: Ar=2-thienyl, Ar′=Ph;b: Ar=p-MeC6H4, Ar′=Ph) in the solid state gives cyclobutane dimers (2) in good yield. The mass spectra of the dimers, where no fragments derived from dimers with equal groups on adjacent carbons are present, suggest a “truxillic” structure (head to tail dimerization). X-Ray determinations confirm a centrosymmetric arrangement with a D2d symmetry of the cyclobutane ring and a puckering constantϕ=24.0° for (2a) significantly higher than that of (2b) (ϕ=19.2°).
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Amato, M.E., Musumarra, G., Scarlata, G. et al. X-ray structure determination of cyclobutane photodimers from (Z)-α, β-diarylacrylonitriles. Journal of Crystallographic and Spectroscopic Research 19, 791–808 (1989). https://doi.org/10.1007/BF01185347
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DOI: https://doi.org/10.1007/BF01185347