Abstract
Photolysis and thermolysis of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonane 1a– c ( a : Ar= p-MeOC 6H 4, b : Ar= p-MeC 6H 4, c : Ar=Ph) were investigated. ( p-Methoxyphenyl)-substituted 1a underwent a novel photo-initiated O-neophyl-type 1,2-aryl shift to afford 1-( p-methoxyphenyl)oxy-5-( p-methoxyphenyl)-8-oxabicyclo[3.2.1]octane 7a along with a small amount of 1-( p-methoxyphenyl)-3-(2-(4′-methoxyphenyl)tetrahydrofuran-2-yl)propan-1-one 4a through an 1,6-dioxyl diradical intermediate, while the thermolysis mainly afforded the 1,5-di( p-methoxyphenyl)pentan-1,5-dione 5a and 1,4-di( p-methoxyphenyl)butan-1,4-dione 8a .
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