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C 4 ‐CYCLODIMERS OF PSORALEN ENGAGING THE 4′,5′‐ DOUBLE BOND
Author(s) -
Caffieri Sergio,
Dall'acqua Francesco
Publication year - 1987
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1987.tb08400.x
Subject(s) - furocoumarin , furocoumarins , psoralen , pyrone , double bond , chemistry , moiety , furan , cycloaddition , stereochemistry , photoisomerization , photochemistry , dna , organic chemistry , isomerization , biochemistry , catalysis
— By irradiating psoralen (the parent linear furocoumarin) in thin solid film two new fluorescent photodimers. compounds I and II, have been isolated and characterized. Unlike previously isolated dimers of furocoumarins which showed a ‘pyrone‐pyrone’ structure involving in the C 4 ‐cycloaddition the 3,4‐double bond of the furocoumarinic moiety, the new dimers show respectively a ‘furan‐furan’ and a ‘furan‐pyrone’ structure, involving therefore the 4′,5′‐double bond. By analogy with the photocycloaddition reactions between furocoumarins and pyrimidine bases of DNA, in this case too the 4′,5′‐double bond of the furocoumarin can be involved. The experimental conditions, however, in which irradiation is carried out play an important role.