Cyсlopentadienone and Pyrone Derivatives as Precursors of Electron-Deficient Cycloheptatrienes. Quantum Chemical Investigation and Synthesis

Cyсlopentadienone and Pyrone Derivatives as Precursors of Electron-Deficient Cycloheptatrienes. Quantum Chemical Investigation and Synthesis Full article

Journal

Synthesis-Stuttgart
ISSN: 1437-210X , E-ISSN: 0039-7881

Output data

Year: 2024, Volume: 56, Number: 16, Pages: 2581-2587 Pages count : 7 DOI: 10.1055/a-2317-6659

Authors

Sokolova Alena D. ¹ , Belyy Alexander Yu. ¹ , Salikov Rinat F. ^1,2 , Platonov Dmitry N. ¹ , Tomilov Yury V. ¹

Affiliations

1	Russian Academy of Sciences, FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moskva, Russian Federation
2	Department of Chemistry, National Research University Higher School of Economics, Moskva, Russian Federation

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.

Sokolova A.D. , Belyy A.Y. , Salikov R.F. , Platonov D.N. , Tomilov Y.V.
Cyсlopentadienone and Pyrone Derivatives as Precursors of Electron-Deficient Cycloheptatrienes. Quantum Chemical Investigation and Synthesis
Synthesis-Stuttgart. 2024. V.56. N16. P.2581-2587. DOI: 10.1055/a-2317-6659 WOS Scopus OpenAlex

≡ Web of science:	WOS:001220696200001
≡ Scopus:	2-s2.0-85192262043
≡ OpenAlex:	W4396517276