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

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...

Full description

Saved in:
Bibliographic Details
Published in:Helvetica chimica acta 2008-09, Vol.91 (9), p.1662-1669
Main Authors: Malashikhin, Sergey A., Linden, Anthony, Heimgartner, Heinz, Rodina, Ludmila L., Nikolaev, Valerij A.
Format: Article
Language:English
Subjects:
4-diazo-2
5-tetrahydro
Diazo compounds
Diazo transfer
Furan-3-one
Furan‐3‐one, 4‐diazo‐2,3,4,5‐tetrahydro
X-Ray crystallography
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.200890182