Abstract
The synthesis of 5-diazo-5-[13C]-homoadamantan-4-one (12) is achieved by ring expansion of adamantanone with 13C-labelled diazomethane, conversion of the resulting 4-[13C]-homoadamantan-4-one (10) to the hydroxymethylene compound (11), followed by deformylative diazo group transfer reaction. The photolysis of 12 with pyrex filtered UV-light in dioxane-water (10:1) yields adamantan-2-carboxylic acid containing all the label in the 2-position of the adamantane skeleton. The total absence of isotope scrambling excludes the intermediate formation of the polycyclic oxiren (16) (Scheme 3).
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