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Synthesis and Structures of Two Isomeric 4-Diazo-2,3,4,5-tetrahydrofuran-3-ones

✍ Scribed by Sergey A. Malashikhin; Anthony Linden; Heinz Heimgartner; Ludmila L. Rodina; Valerij A. Nikolaev

Publisher: John Wiley and Sons
Year: 2008
Tongue: German
Weight: 214 KB
Volume: 91
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200890182

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✦ Synopsis

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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