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It has been reported that tertiary radicals like 2-cyanoprop-2-yl add to 1,4-di-t-butyl-2- nitrosobenzene 2 at the N and O atoms of the nitroso group. In contrast, treatment of the the analogous nitrosobenzene, 2-(4-t-butyl-2-nitrosophenyl)-2-methylpropanoic acid 12, with azobisisobutyronitrile in boiling benzene afforded a 1,6-addition product, 2-(5-t-butyl-1-(1- cyano-1-methylethoxy)imino-4-(1-cyano-1-methylethyl)cyclohexa-2,5-dien-2-yl)-2-methyl- propanoic acid 16 as the sole isolable product.

Anomalous addition of 2-cyanoprop-2-yl radicals to 2-(4-t-butyl-2-nitrosophenyl)-2-methylpropanoic acid