On irradiation in methanol, phenoxyacetonitrile (PhO·CH2·CN) underwent rearrangement to o-hydroxybenzyl cyanide and p-hydroxybenzyl cyanide. Other aryloxyacetonitriles (ArO·CH2·CN : Ar =p-tolyl, p-methoxyphenyl, 3,5- and 2,6-xylenyl) behaved similarly. Ethyl N-methylanilinoacetate (PhNMe·CH2·CO2Et) yielded N-methyloxindole on irradiation in methanol.
K. J. S. Arora, M. K. M. Dirania and J. Hill, J. Chem. Soc. C, 1971, 2865 DOI: 10.1039/J39710002865
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