PEROXIDES OF ELEMENTS OTHER THAN CARBON .15. AUTOXIDATION OF EPIMERIC TRINORBORNYLBORANES

Three epimeric mixtures of trinorbornylboranes have been prepared, in which the percentages of exo- and endonorbornyl groups are 99.2 and 0.8%, 66 and 34%, and 14 and 86%, respectively. All three react with oxygen to give norbornylbis(norbornylperoxy)borane containing about 76% exo- and 24% endo-norbornyl-oxygen links, and the reactions are inhibited by galvinoxyl, copper NN-dibutyldithiocarbamate, and phenothiazine. It is proposed that the autoxidations follow a homolytic chain mechanism involving a common norbornyl radical.