Issue 20, 2013
From the journal:

RSC Advances

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

Axel G. Griesbeck,*a   Viktor Schlundta  and  Jörg M. Neudörfla  

* Corresponding authors

a Department of Chemistry, University of Cologne, Greinstr. 4, D-50939 Köln, Germany
E-mail: griesbeck@uni-koeln.de
Fax: +49-221-4705057

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

DOI
https://doi.org/10.1039/C3RA40555A
Article type
Communication
Submitted
31 Jan 2013
Accepted
20 Mar 2013
First published
21 Mar 2013

RSC Adv., 2013,3, 7265-7270

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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

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

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