Reversible Migrations of Nitro Group in a Methyltetramethoxycarbonylcyclopentadiene System View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2018-04

AUTHORS

G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin

ABSTRACT

Quantum chemical calculations by the density functional theory method at the B3LYP/6-311++G** level have shown that 5-nitro-5-methyl-1,2,3,4-tetramethoxycarbonylcyclopentadiene (1) and 5-nitro-2-methyl- 1,3,4,5-tetramethoxycarbonylcyclopentadiene (2) undergo interconversion by consecutive 1,5-sigmatropic shifts via the formation of an unstable isomer, 5-nitro-1-methyl-2,3,4,5- tetramethoxycarbonylcyclopentadiene (3), rather than through the NMR-detected 1,3-shift of the nitro group over the cyclopentadiene ring perimeter. According to calculations in the gas phase, isomer 3 is by ΔEZPE of 3.6 kcal/mol less stable than isomer 1, while the activation barrier of the stepwise 1 → 2 process is 24.5 kcal/mol, which agrees well with NMR data (ΔG25C≠, chlorobenzene, 26.5 kcal/mol). More... »

PAGES

53-57

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s0012500818040067

DOI

http://dx.doi.org/10.1134/s0012500818040067

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1104139014


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