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A novel photorearrangement of (coumarin-4-yl)methyl phenyl ethers

Paper ID Volume ID Publish Year Pages File Format Full-Text
27825 44044 2009 9 PDF Available
A novel photorearrangement of (coumarin-4-yl)methyl phenyl ethers

In the present study, we describe synthesis and photochemical behaviour of the coumarinylmethyl phenyl ethers 1 and 6–10. Irradiation of the compounds in polar solvents leads to o-, p- and m-hydroxybenzyl substituted coumarins as main products. A side reaction is the photosolvolysis of the ethers that gives the (coumarin-4-yl)methyl alcohol and the corresponding phenol. Detailed studies of the quantum yields and product distributions upon irradiation of 6 as a function of the solvents are indicative of a dominant role of an ionic pathway in photochemical conversions. The found photochemical rearrangement is a useful tool for the preparation of hydroxylated 4-benzylcoumarins. A series of such compounds have been synthesised.

Flash photolysis; Photochemical rearrangement; Coumarin; Synthesis
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A novel photorearrangement of (coumarin-4-yl)methyl phenyl ethers
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 208, Issues 2–3, 15 December 2009, Pages 171–179
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Physical Sciences and Engineering Chemical Engineering Bioengineering