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Photoinduced Electron Transfer (PET) Cyclization and Photooxygenation of 2,6‐Diaryl‐1,6‐heptadienes and 2,7‐Diaryl‐1,7‐octadienes
Author(s) -
Griesbeck Axel G.,
Sadlek Oliver,
Polborn Kurt
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960414
Subject(s) - photooxygenation , chemistry , cyclobutanes , photochemistry , acetonitrile , electron transfer , photoinduced electron transfer , irradiation , oxygen , medicinal chemistry , singlet oxygen , cyclobutane , organic chemistry , ring (chemistry) , physics , nuclear physics
The 2,6‐diaryl‐substituted 1,6‐heptadienes 3a – c and the 2,7‐diaryl‐substituted 1,7‐octadienes 4a – b were cleanly converted into the corresponding anellated cyclobutanes 5 and 6 , resp., when irradiated under photoelectron‐transfer conditions (9,10‐dicyanoanthracene in acetonitrile). Only for 4c did the rearranged compound 7c become the dominant photoproduct. Oxygen trapping experiments with formation of endoperoxides 8 , 9 were successful in the case of the electron‐rich substrates 3b , c and 4c .