Abstract
The first dipolar spiro-σ-complexes with a superelectrophilic dinintrobenzofuroxan fragment and tropolone systems with diastereotopic substituents were synthesized. The kinetics of their enantiotopomerization, which occursvia cleavage-formation of the Cspiro-heteroatom bond, was studied by dynamic1H NMR. The stereorigidity of dinitrobenzofuroxan spiro-complexes in this degenerated process increases in the series: tropolone<aminotropone<aminothiotropone≈aminotroponimine. The two last posses the highest kinetic stability compared to all known zwitterionic spiro-complexes.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1509–1512, August, 1997.
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Kurbatov, S.V., Budarina, Z.N., Vaslyaeva, G.S. et al. Dipolar spirocyclic σ-complexes based on of 4,6-dinitrobenzofuroxan. Russ Chem Bull 46, 1445–1448 (1997). https://doi.org/10.1007/BF02505683
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DOI: https://doi.org/10.1007/BF02505683