Caging of carbonyl compounds as photolabile (2,5-dihydroxyphenyl)ethylene glycol acetals.
Aldehydes and ketones caged as 4-(2,5-dihydroxyphenyl)-1,3-dioxolanes are efficiently (Phi = 0.1-0.2) released in a good to excellent chemical yield upon irradiation with 300 nm light. Caged carbonyl compounds are prepared by their acetalization with (2,5-dimethoxyphenyl)ethylene glycol followed by oxidative demethylation to produce corresponding (1,3-dioxolane-4-yl)-1,4-benzoquinones. The latter acetals are photochemically inert but can be converted into photolabile hydroquinones by mild reduction in situ.
Kostikov
Alexey P
AP
Department of Chemistry, University of Georgia, Athens, Georgia 30602, USA.
Malashikhina
Natalia
N
Popik
Vladimir V
VV
D000080:Acetals / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D019855:Ethylene Glycol / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D010782:Photolysis; D013056:Spectrophotometry, Ultraviolet
D000080:Acetals; D000447:Aldehydes; D007659:Ketones; D019855:Ethylene Glycol