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

The Journal of Organic Chemistry
Alexey P KostikovVladimir V Popik

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.

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Oct 23, 2008·Organic Letters·Alexey P Kostikov, Vladimir V Popik

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Citations

Sep 17, 2016·Journal of the American Chemical Society·Ramsey D HannaPaul E Floreancig
Nov 4, 2016·The Journal of Physical Chemistry. B·Lili DuDavid Lee Phillips
May 12, 2015·Chemical Society Reviews·Raffaello Papadakis, Henrik Ottosson
Mar 20, 2020·Chemistry : a European Journal·Mauricio Lineros-RosaVirginie Lhiaubet-Vallet
May 1, 2018·Organic & Biomolecular Chemistry·Yuki TakedaTadashi Katoh
Dec 24, 2018·Organic & Biomolecular Chemistry·Koichi NaritaTadashi Katoh
Jun 12, 2010·The Journal of Organic Chemistry·Alexander G RussellJohn S Snaith
Sep 25, 2010·Journal of the American Chemical Society·Daniela VergaMauro Freccero
May 27, 2011·The Journal of Organic Chemistry·Lei ZhouPengfei Wang
Mar 5, 2011·The Journal of Organic Chemistry·Haishen YangPengfei Wang
Jul 19, 2014·The Journal of Organic Chemistry·Emmanuel E Nekongo, Vladimir V Popik

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