ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Photochemical Reactions of Arylglycidyl EthersThe absorption, fluorescence and phosphorescence spectra, respectively, of arylglycidyl ether 1 correspond to those of other alkyl aryl ethers. Also the photolysis product distribution (λ = 254 nm) is in agreement with a normal ether photolysis. Furthermore, photoinduced epoxy ring opening takes place giving homopolyaddition oligomers and in methanolic solution also CH3OH addition products. These reactions can be explained using the model of bichromophoric molecules with the ArO-chromophore as donor and the epoxy ring as acceptor. The calculations based on this model are in agreement with the experimental data. In the aromatic nucleus halogene substituted 1 were dehalogenated with high quantum yield (0.25 in the case of bromo substituted compound 1g). The quantum yields of the ArO-C-bond scission are about 0.08 independently of the aromatic ring substituents. As indicated by sensitization and quenching experiments, respectively, with aromatic hydrocarbons the photo reactions proceed via S1 state. It was found that phenol quenches the photodegradation of 1 very efficiently. Excited methyl phenyl glycerol ether 5a reacts with phenyl glycidylether 1a in its ground state producing oligomers.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19853270412
