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Issue 20, 2013
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Functionalized polar 1,2,4-trioxanes as building blocks by singlet oxygenation of 4-hydroxy tiglic acid using the solvent deuterium isotope trick

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Abstract

The substrate 4-hydroxy tiglic acid (1), which has low singlet oxygen reactivity, is converted to the 1,2-hydroperoxyalcohol 2 by photooxygenation in deuterated solvents and used for subsequent BF3-catalyzed peroxyacetalizations with acyclic and cyclic ketones. This route enables the synthesis of water-soluble trioxanes that are versatile building blocks for further functionalization, e.g. ester and amide formation.

Graphical abstract: Functionalized polar 1,2,4-trioxanes as building blocks by singlet oxygenation of 4-hydroxy tiglic acid using the solvent deuterium isotope trick

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Article information


Submitted
31 Jan 2013
Accepted
20 Mar 2013
First published
21 Mar 2013

RSC Adv., 2013,3, 7265-7270
Article type
Communication

Functionalized polar 1,2,4-trioxanes as building blocks by singlet oxygenation of 4-hydroxy tiglic acid using the solvent deuterium isotope trick

A. G. Griesbeck, V. Schlundt and J. M. Neudörfl, RSC Adv., 2013, 3, 7265
DOI: 10.1039/C3RA40555A

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