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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

✍ Scribed by Griesbeck, Axel G. ;Sadlek, Oliver ;Polborn, Kurt

Book ID: 102904274
Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 502 KB
Volume: 1996
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199619960414

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✦ Synopsis

Abstract

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.

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