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On the photooxygenation and autoxidation of dipyrrylmethenes and dipyrrylmethanes
Author(s) -
Norris R. D.,
Lightner D. A.
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160214
Subject(s) - photooxygenation , chemistry , autoxidation , methanol , solvent , photochemistry , singlet oxygen , organic chemistry , oxygen
The dye‐sensitized photooxygenations of 4,4′‐diethyl‐3,5,3′5′‐tetramethyldipyrrylmethene and 4,4 ‐diethyl‐3,5,3′5‐tetramethyldipyrrylmethane have been investigated in neutral, basic and acidic methanol solution. Several photoproducts are common to the photooxygenation of both substrates. The dipyrrylmethene was detected as an intermediate in the photooxygenation of the dipyrrylmethane; however, it was determined not to be an important precursor to monopyrrole products. Autoxidations of the two dipyrrole compounds were also investigated and were found to be slower than the corresponding photooxygenation. Autoxidation and photooxygenation were both found to be faster in basic than in acidic methanol with the dipyrrylmethane faster than with the dipyrrylmethene in the same solvent.