European Journal of Organic Chemistry | VOL. 1976
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β‐Polycarbonylverbindungen, X1 Kondensationsprodukte der Pentacetsäure – Addition von Organometallverbindungen an Pyrone

Publication Date Oct 8, 1976

Abstract

Ather 7 des Triacetsaurelactons reagieren mit dem Anion des Essigsaure-tert-butylesters auf dem Orsellinsaurekondensationsweg zuu Everninsaure-tert-butylester (5a) und den Dianionen des Acetessigesters und Acetylacetons sowie dem Trianion des Diacetylacetons nach dem Prinzip der Kotaninkondensation zu den Chronionen 11, 8 bzw. 12 uber Derivate der Pentacetsaure. Ausgehend von dem Benzylather 7 b des Triacetsaurelactons und dem Dianion des Acetessigesters konnte als nicht aromatisches Zwischenprodukt das cyclische Hemiacetal 10 b isoliert werden. Triacetsaurelacton (7c) reagiert mit dem Dianion des Acetessigesters nach dem Prinzip der „ Citrininkondensation ” zum Acetylderivat 9c des Orsellinsaurealthylesters.p-Polycarbonyl Compounds, X 1). -Condensation Products of Pentacetic Acid-Addition of Organometallic Compounds to PyronesThe anion of tert-butyl acetate reacts with ethers 7 of triacetic acid lactone via orsellinic acid type condensation to give tert-butyl everninate (5a). The dianions of ethyl acetoacetate and acetylacetone and the trianion of diacetylacetone undergo cotanin type condensation with 7 to give the chromones 11, 8 and 12, respectively, via pentacetic acid derivatives. On reaction of the benzyl ether 7b of triacetic acid lactone with the dianion of ethyl acetoacetate the cyclic hemiacetal 10b can be isolated as non-aromatic intermediate. -Triacetic acid lactone (7c) reacts with the dianion of ethyl acetoacetate via citrinin type condensation to give the acetyl derivative 9c of ethyl orsellinate.

Concepts
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Triacetic Acid Lactone
Ethyl Acetoacetate
Citrinin
Pentacetic Acid
Type Condensation
Acetoacetate
Nach Dem Prinzip Der
Lactone
Derivative
Condensation Products

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