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CHEMISTRY OF SINGLET OXYGEN—48. ISOLATION and STRUCTURE OF THE PRIMARY PRODUCT OF PHOTOOXYGENATION OF 3,5‐DI‐t‐BUTYL CATECHOL
Author(s) -
Jensen Frank,
Foote ChristopherS.
Publication year - 1987
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1987.tb04776.x
Subject(s) - photooxygenation , singlet oxygen , chemistry , catechol , photochemistry , substituent , oxygen , singlet state , organic chemistry , excited state , physics , nuclear physics
The dye‐sensitized photooxygenation of t ‐butyl substituted catechols has been investigated. The primary product from 3,5‐di‐ t ‐butyl catechol has been isolated and shown to be a hydroperoxydienone by single crystal X‐ray diffraction. The absence of sensitizer effects and the faster reaction rate in polar solvents suggest that the reaction proceeds with singlet oxygen as the primary oxygenating species. Charge‐transfer or full electron‐transfer from the catechol to singlet oxygen is probably involved. Substituent effects are in agreement with this mechanism. The products from thermal breakdown of the hydroperoxydienone are inconsistent with a Baeyer‐Villiger mechanism.