An Exception to the Bredt Rule in the Photoenolization of 4‐Benzoyl[2.2]paracyclophane | Zendy

Hopf Henning | Zendy; Laue Thomas | Zendy; Zander Maximilian | Zendy

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An Exception to the Bredt Rule in the Photoenolization of 4‐Benzoyl[2.2]paracyclophane

Author(s) -

Hopf Henning,

Laue Thomas,

Zander Maximilian

Publication year - 1991

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199104321

Subject(s) - benzophenone , isomerization , photochemistry , derivative (finance) , chemistry , methanol , fluorescence , organic chemistry , physics , catalysis , quantum mechanics , financial economics , economics

Extreme deformation of the ethano bridge occurs during the isomerization of the chiral benzophenone derivative 1 to the yellow, reactive ortho ‐quinoid system 2 on irradiation. This is proved unambiguously by photoenolization experiments in [D 4 ]methanol. Whereas 2 is interesting as a reactive preparative intermediate, the fluorescence properties of 1 suggest a possible application as triplet sensitizer in photochemical reactions.

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