Universität zu Köln

Eske, Angelika, Ecker, Sabrina, Fendinger, Carolina, Goldfuss, Bernd ORCID: 0000-0002-1814-8818, Jonen, Matthis, Lefarth, Jens, Neudoerfl, Joerg-M., Spilles, Matthias and Griesbeck, Axel G. (2018). Spirofused and Annulated 1,2,4-Trioxepane-, 1,2,4-Trioxocane-, and 1,2,4-Trioxonane-Cyclohexadienones: Cyclic Peroxides with Unusual Ring Conformation Dynamics. Angew. Chem.-Int. Edit., 57 (42). S. 13770 - 13775. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3773

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Abstract

C3- or C4-hydroxyalkylated phenols are highly reactive towards peroxidation with oxone, which results in the formation of tertiary C3 hydroperoxides. This reaction can also be performed with photochemically generated singlet oxygen. However, other characteristic singlet oxygen reactions do not proceed with caroate. The initially formed hydroperoxides cyclize in the presence of a Lewis acid catalyst based on boron, indium, or iron to give spiroannulated peroxides. These exhibit restricted ring inversion whereas larger nine-membered-ring peroxides are thermally less stable and show higher ring flexibility (according to NMR analysis).

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Eske, Angelika UNSPECIFIED UNSPECIFIED UNSPECIFIED Ecker, Sabrina UNSPECIFIED UNSPECIFIED UNSPECIFIED Fendinger, Carolina UNSPECIFIED UNSPECIFIED UNSPECIFIED Goldfuss, Bernd UNSPECIFIED orcid.org/0000-0002-1814-8818 UNSPECIFIED Jonen, Matthis UNSPECIFIED UNSPECIFIED UNSPECIFIED Lefarth, Jens UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Spilles, Matthias UNSPECIFIED UNSPECIFIED UNSPECIFIED Griesbeck, Axel G. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-169287
DOI:	10.1002/anie.201807485
Journal or Publication Title:	Angew. Chem.-Int. Edit.
Volume:	57
Number:	42
Page Range:	S. 13770 - 13775
Date:	2018
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3773
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language KETONE-CATALYZED DECOMPOSITION; SINGLET OXYGEN; ORGANIC PEROXIDES; ANTICANCER AGENTS; ANTIMALARIAL AGENTS; MEDICINAL CHEMISTRY; POTENT ANTIMALARIAL; CHINESE MEDICINE; NATURAL-PRODUCTS; CAROS ACID Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/16928