N-tert-Butoxy-N-tert-alkylaminyls. A New Class of Persistent Radicals

Article abstract of DOI:10.1021/ja00531a024

N-tert-Butoxy-N-tert-butylaminyl (1^.) and three related radicals have been generated from their parent hydroxylamines in hydrocarbon solution.In the absence of oxygen these radicals are extremely persistent.Their electronic structures, as indicated by their EPR parameters (a^14N, a^17O, and a^13C, all determined without isotopic enrichment) and the N-H bond strength in 1-H (measured as 81.0 kcal/mol), show that the effectiveness of conjugative electron delocalization is reduced relative to that in the isomeric nitroxides.This effect is attributed to the greater electro negativity of oxygen compared with nitrogen.