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Demonstration of the Participation of Free Radicals in the Rearrangement of Benzyl Phenyl Ether

Abstract

IT has been shown previously1 that when benzyl phenyl ether is heated in quinoline at about 250°, the normal rearrangement of the ether to o- and p-benzyl phenols is accompanied by the formation of benzyl-quinolinos and of toluene. It is now found that hydroxyphenyl quinolines are also products of this reaction, and that it is possible, by a careful control of the experimental conditions, to increase very considerably the yields of benzylquinolines and hydroxyphenyl quinolines at the expense of the normal products of the rearrangement.

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References

  1. Hickinbottom, NATURE, 142, 830 (1938).

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  2. Bradley and Robinson, J. Chem. Soc., 1254 (1932).

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HICKINBOTTOM, W. Demonstration of the Participation of Free Radicals in the Rearrangement of Benzyl Phenyl Ether. Nature 143, 520 (1939). https://doi.org/10.1038/143520b0

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