Gas phase generation and reactions of o-dialkylaminobenzyl and o-dialkylaminophenoxyl radicals

Abstract

Generation of the title radicals was effected by flash vacuum pyrolysis of benzyl phenyl ethers, and O-allyl ethers, respectively. The major products are formed by a multi-step sequence involving (i) intramolecular hydrogen transfer from the alkylamino group to the initial radical centre, (ii) rearrangement of the resulting aminoalkyl radical, and (iii) expulsion of the nitrogen residue to give a benzyl radical which leads to products.