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Synthesis and Structures of Two Isomeric 4‐Diazo‐2,3,4,5‐tetrahydrofuran‐3‐ones
Author(s) -
Malashikhin Sergey A.,
Linden Anthony,
Heimgartner Heinz,
Rodina Ludmila L.,
Nikolaev Valerij A.
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890182
Subject(s) - chemistry , tetrahydrofuran , diazo , azide , crystal structure , stereochemistry , medicinal chemistry , organic chemistry , solvent
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.