Synthesis and Structures of Two Isomeric 4‐Diazo‐2,3,4,5‐tetrahydrofuran‐3‐ones | Zendy

Malashikhin Sergey A. | Zendy; Linden Anthony | Zendy; Heimgartner Heinz | Zendy; Rodina Ludmila L. | Zendy; Nikolaev Valerij A. | Zendy

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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.

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