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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.