Substituent effects on the 4π + 2π cycloadditions of 4H-pyran-4-one derivatives

Mónika Rudas, Imre Fejes, Miklós Nyerges, A. Szöllösy, L. Tőke, Paul W. Groundwater

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

The simple y-pyranones 4,5, and 6 undergo 4π + 2π cycloaddition reactions with Danishefsky's diene 8 and azomethine ylides 12,16, and 25 to give a range of cycloadducts. The position of the electron-withdrawing group is the decisive factor in these reactions, with the 2-substituted derivatives 5 and 6 being less reactive than the 3-substituted γ-pyranone 4. The esters, 4 and 5, react via addition across the 2,3-C=C bond of the pyranone ring, whilst the aldehyde 6 reacts via addition across the C=O of the carbaldehyde group.

Original languageEnglish
Pages (from-to)1167-1172
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number9
Publication statusPublished - 1999

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Pyrans
Cycloaddition
Aldehydes
Esters
Derivatives
Electrons
azomethine

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry

Cite this

Substituent effects on the 4π + 2π cycloadditions of 4H-pyran-4-one derivatives. / Rudas, Mónika; Fejes, Imre; Nyerges, Miklós; Szöllösy, A.; Tőke, L.; Groundwater, Paul W.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 9, 1999, p. 1167-1172.

Research output: Contribution to journalArticle

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