Chemical transformations of tetracyclo[3.3.1.13,7.01,3]decane (1,3-dehydroadamantane): III. Reactions of 1,3-dehydroadamantane with isothiocyanates

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1,3-Dehydroadamantane reacted with phenyl isothiocyanate at 120–130°C under solvent-free conditions to give 4-(adamantan-1-yl)phenyl isothiocyanate. The selectivity of its reactions with benzyl and phenethyl isothiocyanates in which the isothiocyanato group is separated from the benzene ring by methylene or ethylene bridge was lower, and adamantylation of the para position of the benzene ring was accompanied by adamantylation of the methylene groups.