Intramolecular Proton Transfer in Photohydration Reactions

Article abstract of DOI:10.1021/ja00280a028

The photohydration by intramolecular proton transfer of compounds 1-12 has been studied.The non-nitro-substituted o-hydroxystyrenes photohydrate cleanly via the Markovnikov addition of water to afford the 1-arylethanols.The nitro-substituted o-hydroxystyrenes showed no dependence of product quantum yield with change in pH.The products isolated and identified in this case were the corresponding 2-(2-hydroxyphenyl)ethanols.Compounds with α substituents showed evidence of an increased interaction between the hydroxyl group and the ? orbitals of the vinyl moiety.The absolute quantum yields for 1 and 9 were estimated and used to calculate the effective molarities, EM = 1E-2 and 2.6, respectively.