Carbamoyl radicals from carbamoylxanthates: a facile entry into isoindolin-1-ones

It has been found that carbamoylxanthates derived from secondary t-butyl amines are stable compounds which function as efficient sources of carbamoyl radicals. The carbamoylxanthates derived from t-butylbenzylamines can be efficiently transformed into 2-t-butylisoindolin-1-ones via an oxidative radical cyclization process. The carbamoylxanthates derived from N-t-butylamino olefins underwent the expected cyclization/xanthate-transfer process to afford the corresponding pyrrolidones and piperidones under thermally induced DLP fragmentation conditions and in the presence of catalytic Et3B in air, at room temperature.