Beilstein J. Org. Chem.2011,7, 127–134, doi:10.3762/bjoc.7.18
-controlled formation of the corresponding triplet 1,4-biradical and high stereocontrol due to SOC-controlled crossing from the triplet to the singlet surface [4][5].
Reaction behavior of the photoproducts 9a–c
All bicyclic oxetanes obtained in the analytical photochemical experiments as well as in
Beilstein J. Org. Chem.2007,3, No. 14, doi:10.1186/1860-5397-3-14
can be visualized as having occurred through an initial abstraction of the O-methine proton of cycloalkenyl group by the excited carbonyl of the pyrone moiety to produce 1,4-biradical 8. The photoproduct 5 (a, b, c, d), is then formed through bond formation between the alkoxy radical and furan (8
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Graphical Abstract
Scheme 1:
Synthesis of 3-Cycloalkenyloxybenzopyrans.