Generation of 1-aryl-3-methoxycarbonylnitrilimines and their reaction with halogen-containing unsaturated compounds

Thermal decomposition of 1-(4-methoxyphenyl)- and 1-(4-fluorophenyl)hepta(methoxycarbonyl)-3a,7a-dihydroindazoles at 135 °C in the presence of allyl or propargyl halides leads to the elimination of hexamethyl benzenehexacarboxylate and the formation of the corresponding pyrazolines or pyrazoles as t...

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Published inRussian chemical bulletin Vol. 61; no. 6; pp. 1138 - 1147
Main Authors Tomilov, Yu. V., Platonov, D. N., Okonnishnikova, G. P., Novikov, R. A., Volchkov, N. V.
Format Journal Article
LanguageEnglish
Published Boston Springer US 01.06.2012
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Inorganic Chemistry
Organic Chemistry
thermolysis
pyrazolines
1,3-dipolar addition
pyrazoles
3a,7a-dihydroindazoles
nitrilimines
hydrazones
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Summary:Thermal decomposition of 1-(4-methoxyphenyl)- and 1-(4-fluorophenyl)hepta(methoxycarbonyl)-3a,7a-dihydroindazoles at 135 °C in the presence of allyl or propargyl halides leads to the elimination of hexamethyl benzenehexacarboxylate and the formation of the corresponding pyrazolines or pyrazoles as the products of 1,3-dipolar cycloaddition of 1-aryl-3-methoxycarbonylnitrilimines to the multiple bonds of the substrates used. In the case of vinyl halides, the products of the target reactions are either obtained in low yields or nonexistent, with a side conversions taking place instead. Thus, for example, in the case of 1,1-dichloro-4-methylpenta-1,3-diene, besides hexamethyl benzenehexacarboxylate, 3,5,5-trichloro-2-methylpent-4-en-2-ol and arylchlorohydrazones MeO 2 CC(Cl)=N-NHAr were unexpectedly isolated as the main products, as well.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-012-0155-x