@article{SchaalKotzurDekowskietal.2009, author = {Schaal, Janina and Kotzur, Nico and Dekowski, Brigitte and Quilitz, Jana and Klimakow, Maria and Wessig, Pablo and Hagen, Volker}, title = {A novel photorearrangement of (coumarin-4-yl)methyl phenyl ethers}, issn = {1010-6030}, doi = {10.1016/j.jphotochem.2009.09.012}, year = {2009}, abstract = {In the present study, we describe synthesis and photochemical behaviour of the coumarinylmethyl phenyl ethers 1 and 6-10. Irradiation of the compounds in polar solvents leads to o-, p- and m-hydroxybenzyl substituted coumarins as main products. A side reaction is the photosolvolysis of the ethers that gives the (coumarin-4-yl)methyl alcohol and the corresponding phenol. Detailed studies of the quantum yields and product distributions upon irradiation of 6 as a function of the solvents are indicative of a dominant role of an ionic pathway in photochemical conversions. The found photochemical rearrangement is a useful tool for the preparation of hydroxylated 4-benzylcoumarins. A series of such compounds have been synthesised.}, language = {en} }