Thermolysis of furoxans annulated with five-membered carbocycles in the presence of dipolarophiles |
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Authors: | A S Kulikov M A Epishina I V Ovchinnikov N N Makhova |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | The conditions for the thermolysis of furoxans annulated with differently strained five-membered carbocycles (cyclopentafuroxan
1, norbornenofuroxan 2, and acenaphthofuroxan 3) to bis(nitrile oxides) in the presence of various dipolarophiles (diethyl acetylenedicarboxylate, benzoylformonitrile, and
ethoxycarbonylformonitrile) were optimized. It was found that the reactivities of the above furoxans as sources of bis(nitrile
oxides) decrease in the order 2 > 1 > 3. Among the furoxans studied, only norbornenofuroxan 2 can be recommended as a possible cross-linking reagent for polymers. The formation of di-N-oxides of 3,4-bis(cyanopropyl)-, 3,4-bis(cyanocyclopentyl)-, and 3,4-bis(cyanonaphthyl)furoxans was detected. They resulted
from intermolecular cyclodimerization of bis(nitrile oxides) initially formed in the thermolysis of furoxans 1–3.
Dedicated to Academician V. A. Tartakovsky on the occasion of his 75th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1521–1528, August, 2007. |
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Keywords: | furoxans annulated with five-membered carbocycles thermolysis bis(nitrile oxides) dipolarophiles 1 3-cycloaddition cross-linking |
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