Stannylated α-pyrones: Synthesis, halogenation and destannylation reactions

Ethynyltributyltin undergoes inverse type [4+2] cycloadditions with various 1,3,4-oxadiazin-6-ones to afford two regioisomeric stannylated α-pyrones, which can be separated by flash column chromatography. Exposure of the stannanes to elemental halogens in chloroform or THF as solvent yields the corr...

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Bibliographic Details
Published in:Tetrahedron 1998-10, Vol.54 (42), p.12807-12822
Main Authors: Sauer, Jürgen, Heldmann, Dieter K., Range, Klaus-Jürgen, Zabel, Manfred
Format: Article
Language:English
Subjects:
Alkynes
compounds
Cycloadditions
Pyrones
Tin
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Summary:Ethynyltributyltin undergoes inverse type [4+2] cycloadditions with various 1,3,4-oxadiazin-6-ones to afford two regioisomeric stannylated α-pyrones, which can be separated by flash column chromatography. Exposure of the stannanes to elemental halogens in chloroform or THF as solvent yields the corresponding halogeno pyrones. A general exception of this reaction type is also described. Destannylation with dry hydrogen chloride furnishes 3,6-disubstituted α-pyrones. The synthesis of the title compounds from 1,3,4-oxadiazin-2-ones and some possible applications are reported.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)00754-6