Caging of carbonyl compounds as photolabile (2,5-dihydroxyphenyl)ethylene glycol acetals

J Org Chem. 2009 Feb 20;74(4):1802-4. doi: 10.1021/jo802612f.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemistry*
  • Aldehydes / chemistry*
  • Ethylene Glycol / chemistry*
  • Ketones / chemistry*
  • Photolysis*
  • Spectrophotometry, Ultraviolet

Substances

  • Acetals
  • Aldehydes
  • Ketones
  • Ethylene Glycol