Stannylated alpha-pyrones: Synthesis, halogenation and destannylation reactions

Sauer, Jürgen and Heldmann, Dieter K. and Range, Klaus-Jürgen and Zabel, Manfred (1998) Stannylated alpha-pyrones: Synthesis, halogenation and destannylation reactions. TETRAHEDRON, 54 (42). pp. 12807-12822. ISSN 0040-4020

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Abstract

Ethynyltributyltin undergoes inverse type [4+2] cycloadditions with various 1,3,4-oxadiazin-6-ones to afford two regioisomeric stannylated alpha-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 alpha-pyrones. (C) 1998 Elsevier Science Ltd. All rights reserved.

Item Type: Article
Uncontrolled Keywords: 1,3,4-OXADIAZIN-6-ONES 4,5-DIAZA-ALPHA-PYRONES; CYCLOADDITIONS; NORBORNADIENE; cycloadditions; tin and compounds; alkynes; pyrones
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Anorganische Chemie > Alumni or Retired Professors > Prof. Dr. Klaus-Jürgen Range
Chemistry and Pharmacy > Institut für Organische Chemie
Depositing User: Dr. Gernot Deinzer
Date Deposited: 23 Feb 2023 06:25
Last Modified: 23 Feb 2023 06:25
URI: https://pred.uni-regensburg.de/id/eprint/49438

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