Regioselective functionalisation of triamantane

Abstract

The C18H24 diamondoid hydrocarbon triamantane reacts with bromine largely at the 2-position and with lead tetrabenzoate largely at the 3-position; 2-bromotriamantane can be isomerised to 9-bromotriamantane and the 9-methyl derivative can be obtained directly from a C19H26 precursor by aluminium chloride-catalysed rearrangement.