The first examples of the addition of heterocyclic NH to unactivated olefins

Abstract

Benzotriazole adds to aliphatic open-chain and cyclic alkenes at 80 °C under toluene-p-sulfonic acid catalysis. Terminal aliphatic olefins give solely 2-(benzotriazol-1- and -2-y-1)alkanes, which are stable to acid. In the presence of an excess of acid, all possible non-terminal benzotriazol-1-and -2-y-1 addition products are obtained, owing to a facile migration of the double bond in the starting olefin. Addition also occurs to phenylalkenes with the intervention of some bond migration.