Premium
PSORALEN‐OLEFIN PHOTOPRODUCI'S: FIRST OBSERVATION OF A PHOTO‐ENE REACTION
Author(s) -
Semin David J.,
Winkler Paul C.,
Rowlen Kathy L.
Publication year - 1994
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.1751-1097.1994.tb05089.x
Subject(s) - chemistry , ene reaction , singlet oxygen , olefin fiber , cycloaddition , hydroxymethyl , psoralen , product distribution , yield (engineering) , photochemistry , singlet state , oxygen , organic chemistry , catalysis , excited state , dna , biochemistry , materials science , metallurgy , physics , nuclear physics
Methyl‐substituted psoralens (4′‐(hydroxymethyl)‐4,5′,8‐trimethylpsoralen and 4,5′,8‐trimethylpsoralen) are found to yield an ene product as well as the expected [2+2] cycloaddition product from photochemical reaction with simple olefins. As determined by absorbance, liquid chromatography‐mass spectrometry and nuclear magnetic resonance, both products are formed at the pyrone side of the respective psoralen. The product distribution is dependent on olefin concentration as well as the nature of the olefin. In deoxygenated solutions, cyclic olefins form as much as 50% ene product, while unsubstituted straight‐chain olefins form as little as 3%. In oxygenated solutions, the product distribution is strongly affected by singlet oxygen.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom