Generation of quinone methide from aminomethyl(hydroxy)arenes precursors in aqueous solution

o-Quinone methides (QMs) are an important reactive intermediate for organic synthetic and biological standpoints of view. Photochemical and thermal transformation of N,N-dialkyl-9-aminomethyl-10-phenanthrols and their naphthalene analogs, which act as QM precursors, has been studied. These precursors readily reacted with alkyl vinyl ethers to give 2-alkoxydibenzo[f,h]chroman and 2-alkoxybenzo[f]chroman, respectively. Thermal and photochemical generation of QM was accelerated by the presence of water molecule in reaction solvents and by the formation of anionic micelle and vesicle.