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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