The irradiation of various
types of aromatic ethers with ultraviolet light has been shown to yield o- and
p-substituted phenols, resulting from C-O bond fission followed by
recombination of the two fragments. Also formed in these photolyses was the
parent phenol, produced presumably by abstraction of hydrogen from the solvent
by the aryloxy fragment. The ethers investigated were aryloxyacetic acids,1 allyl aryl ethers,2
benzyl phenyl ether, and diphenyl ether. ��� Mixture experiments have shown that for both
the aryloxyacetic acids and allyl aryl ethers the rearrangement is
intramolecular and most probably proceeds by formation of a radical-pair
enclosed in a solvent cage.
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