Synthesis and thermal transformations of allyl aryl ethers of adamantane series

Allyl aryl ethers of adamantane series were obtained by reacting (E)-1-(adamant-1-yl)-3-bromoprop-1-ene with phenol or ethyl salicylate. The features of thermal transformations of allyl aryl ethers containing bulky adamantane scaffold were investigated. It has been found that the composition of the reaction products is largely dependent on temperature, time and nature of the solvent. When a nucleophilic solvent was used, the reaction proceeded via formal substitution of phenoxy fragment with nucleophilic species prevailing in the reaction medium.