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 in | Russian chemical bulletin Vol. 61; no. 6; pp. 1138 - 1147 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Boston
Springer US
01.06.2012
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Subjects | |
Online Access | Get full text |
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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. |
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ISSN: | 1066-5285 1573-9171 |
DOI: | 10.1007/s11172-012-0155-x |