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Structure and Tautomerism of Cyclopentadiene Derivatives: X. 1,5-Sigmatropic Shifts of the p-Nitrobenzyl Group in Tetramethyl 5-Methylcyclopentadienetetracarboxylate

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Abstract

The reaction of thallium 5-methyl-1,2,3,4-tetrakis(methoxycarbonyl)cyclopentadienide with p-nitrobenzyl bromide gave a mixture of isomeric p-nitrobenzylcyclopentadienes. The isomers were separated, and the structure of each isomer was established by 1H and 13C NMR spectroscopy. 1,5-Sigmatropic shifts of the p-nitrobenzyl group along the cyclopentadienyl ring were revealed, their Gibbs activation energies ΔG ≠120°C ranging from 29.5 to 30.6 kcal/mol.

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Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry, Rostov State University, pr. Stachki 194/2, Rostov-on-Don, 344090, Russia

    I. E. Mikhailov, G. A. Dushenko, I. S. Nikishina & V. I. Minkin

  2. State Research Institute of the Chemistry and Technology of Organometallic Compounds, Moscow, Russia

    A. V. Kisin

Authors
  1. I. E. Mikhailov
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  2. G. A. Dushenko
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  3. I. S. Nikishina
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  4. A. V. Kisin
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  5. V. I. Minkin
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Mikhailov, I.E., Dushenko, G.A., Nikishina, I.S. et al. Structure and Tautomerism of Cyclopentadiene Derivatives: X. 1,5-Sigmatropic Shifts of the p-Nitrobenzyl Group in Tetramethyl 5-Methylcyclopentadienetetracarboxylate. Russian Journal of Organic Chemistry 38, 1449–1455 (2002). https://doi.org/10.1023/A:1022592018924

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