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Synthesis and structures of two isomeric 4-diazo-2,3,4,5-tetrahydrofuran-3-ones


Malashikhin, S A; Linden, A; Heimgartner, H; Rodina, L L; Nikolaev, V A (2008). Synthesis and structures of two isomeric 4-diazo-2,3,4,5-tetrahydrofuran-3-ones. Helvetica Chimica Acta, 91(9):1662-1668.

Abstract

The two regioisomeric 4-diazo-2,3,4,5-tetrahydrofuran-3-ones 6 and 7 were prepared via the common intermediate 2,3,4,5-tetrahydro-2,2-dimethyl-5,5-diphenylfuran-3-one (8). Diazo transfer with 2,4,6-triisopropylbenzenesulfonyl azide yielded 6, whereas 7 was obtained via oxidation of the monohydrazone 12, which was prepared selectively from tetrahydrofuran-3,4-dione 11. The crystal structures of 6 and 7 have been established by X-ray crystallography.

Abstract

The two regioisomeric 4-diazo-2,3,4,5-tetrahydrofuran-3-ones 6 and 7 were prepared via the common intermediate 2,3,4,5-tetrahydro-2,2-dimethyl-5,5-diphenylfuran-3-one (8). Diazo transfer with 2,4,6-triisopropylbenzenesulfonyl azide yielded 6, whereas 7 was obtained via oxidation of the monohydrazone 12, which was prepared selectively from tetrahydrofuran-3,4-dione 11. The crystal structures of 6 and 7 have been established by X-ray crystallography.

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Additional indexing

Other titles:
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:September 2008
Deposited On:06 Feb 2009 11:16
Last Modified:05 Apr 2016 12:57
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.200890182

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