Dipolar spirocyclic σ-complexes based on of 4,6-dinitrobenzofuroxan |
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| Authors: | S V Kurbatov Z N Budarina G S Vaslyaeva N I Borisenko A P Knyazev V I Minkin Yu A Zhdanov L P Olekhnovich |
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| Institution: | (1) Department of Chemistry, Rostov State University, 7 ul. Zorge, 344090 Rostoy-on-Don, Russian Federation;(2) Institute of Physical Organic Chemistry, Rostoy State University, 194/2 ul. Stachki, 344090 Rostov-on-Don, Russian Federation |
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| 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.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1509–1512, August, 1997. |
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| Keywords: | tropolone 4 6-dinitrobenzofuroxan dipolar spiro-σ -complexes enantiotopomerization |
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