
Helvetica Chimica Acta p. 571 - 587 (1980)
Update date:2022-07-30
Topics:
Yoshioka, Michikazu
Ishii, Keitaro
Wolf, Hans Richard
On 1n,?*-excitation (λ>347 nm) citral (5) and the methyl ketone 10 isomerize to compounds A (7, 19) and B(6, 20), whereas the phenyl ketone 11 changes into the isomer 24 of type E. evidence is given that the conversion to A and B may arise from the 3n,?*-state of the 2,6-diene-carbonyl compounds.On 1p,?*-excitation (λ=254 nm) 5 and 10 yield the isomers A (7, 19) and D (18, 22), but no products of type B.Futhermore, conversion of 10 to the isomer 21 of type C is observed.Selective 1?,?*-excitation (λ=254 nm) as well as selective 1n,?*-excitation (λ>347 nm) of the 2,7-diene-carbonyl compounds 12 and 13 give rise to isomerization to the compounds F (25, 28), exclusively.The intramolecular (2+2)-photocycloadditions are shown to be triplet processes.UV.-irradiation (λ>280 nm) of compounds F (25, 28) furnishes the isomeric products G (26, 29) which photoisomerize to oxetanes of type H (27, 30).
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Doi:10.1021/ja00529a027
(1980)Doi:10.1002/asia.201800367
(2018)Doi:10.1055/s-2004-822393
(2004)Doi:10.1248/cpb.28.926
(1980)Doi:10.1081/SCC-120039493
(2004)Doi:10.1021/acs.joc.1c00148
(2021)