Peroxides of elements other than carbon. Part XVI. Autoxidation of the epimeric norbornylmagnesium halides

Abstract

The autoxidation of norborn-2-ylmagnesium bromide (41%exo–59%endo, and ca. 100%endo) and chloride (43%exo–57%endo) gave in all three cases a mixture of norborn-2-ylperoxy-compounds similar to that (76%exo–24%endo) obtained in the autoxidation of exo- or endo-norbornylboranes, where there was independent evidence for a radical chain mechanism. The reaction of the Grignard reagent probably also follows a homolytic mechanism but a carbanion chain cannot be excluded.

The kinetics of the epimerisation of endo-norborn-2-ylmagnesium bromide have been determined.