21898-95-3Relevant articles and documents
Competitive and Regiospecific Bridgehead Substitution in Electrophilic Oxidation Reactions of Homoadamantane
Israel, Robert J.,Murray, Roger K.
, p. 4701 - 4705 (2007/10/02)
Oxidation of homoadamantane with chromic acid, lead tetraacetate, p-nitroperbenzoic acid, or bromine occurs by competitive attack at the C-3 (major) and C-1 (minor) bridgehead positions.In striking contrast, dry ozonation of homoadamantane adsorbed on silica gel leads to regiospecific substitution at the chemically equivalent C-3 and C-6 bridgehead positions.A consequence of this observation is that some 1,3- and 3,6-disubstituted homoadamantanes can be prepared by dry ozonation of suitably substituted homoadamantane derivatives.
