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Photooxygenation of some potentially skin‐photosensitizing furocoumarins: Imperatorin, alloimperatorin and its methyl ether and acetate derivatives
Author(s) -
AbouElzahab Mohamed M.,
Adam Waldemar,
SahaMöller Chantu R.
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101166
Subject(s) - photooxygenation , furocoumarins , chemistry , imperatorin , allylic rearrangement , singlet oxygen , furocoumarin , organic chemistry , ether , photochemistry , biochemistry , high performance liquid chromatography , dna , oxygen , catalysis
The photooxygenation of imperatorin ( 1a ) afforded the corresponding allylic hydroperoxides 2a and 3a in very good yields. Similarly, the photooxygenation of alloimperatorin derivatives 1c , d gave the allylic hydroperoxides 2c , d and 3c , d in quantitative yields. On the other hand, on photooxygenation of alloimperatorin ( 1b ) exclusively the dienone hydroperoxide 4b was obtained. When the reaction time was prolonged, the bis(hydroperoxide) 5b was also formed by successive photooxygenation of 4b .