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Synthesis 2024; 56(16): 2581-2587
DOI: 10.1055/a-2317-6659
DOI: 10.1055/a-2317-6659
paper
Cyсlopentadienone and Pyrone Derivatives as Precursors of Electron-Deficient Cycloheptatrienes: Quantum Chemical Investigation and Synthesis
The work was supported by the Russian Science Foundation (Grant No. 23-73-10181).
Abstract
Unstable tetra(methoxycarbonyl)cyclopentadienone was investigated in the synthesis of electron-deficient cycloheptatrienes via [4+2]-cycloaddition/cycloelimination reaction with cyclopropenes. The use of its stable dimer did not afford the product although similar reactions with alkynes have been reported. Quantum chemical calculation revealed that cyclopentadienone is not generated from the dimer and the reaction with alkynes proceeds via a more complicated cycloelimination/cycloaddition/cycloelimination cascade. However, the formation of cycloheptatrienes was found favorable over the formation of the dimer. Therefore, the trapping of tetra(methoxycarbonyl)cyclopentadienone upon formation was successful to give cycloheptatrienes with five ester groups. The use of methyl coumalate as a four-electron component was successful with cyclopropenes containing only one ester group to afford only two ester groups in the product.
Key words
electron-deficient cycloheptatrienes - cyclopentadienones - cyclopropenes - pyrones - cycloaddition - domino reactionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2317-6659.
- Supporting Information
Publication History
Received: 05 April 2024
Accepted after revision: 30 April 2024
Accepted Manuscript online:
30 April 2024
Article published online:
13 May 2024
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