Journal of Organic Chemistry p. 635 - 640 (1989)
Update date:2022-07-29
Topics: Reactions Products Methyl (E)-2-Cyano-3-(p-substituted-phenyl)acrylates 1-Phenyldiazoethane Secondary Pyrazolines
Nagai, Wakatu
Hirata, Yumiko
In dichloromethane, the reaction of methyl (E)-2-cyano-3-(p-substituted-phenyl)acrylates (2) with 1-phenyldiazoethane (1), prepared from 2 molar equiv of acetophenone hydrazone, produced methyl 2-cyano-4-phenyl-4-(p-substituted-phenyl)-2-pentenoates (3), 1-cyano-1-(methoxycarbonyl)-2-methyl-2-phenyl-3-(p-substituted-phenyl)cyclopropanes (4), and 4-cyano-4-(methoxycarbonyl)-3-methyl-3-phenyl-5-(1-phenyl-1-(p-substituted-phenyl)ethyl)-1-pyrazolines (5).Compounds 5 were found to be derived from compounds 3 and 1.Compounds 5 were different from the primary pyrazolines derived from compounds 1 and 2, both in mode of formation and properties.Compounds 5, when decomposed thermally or photochemically, produced the initial olefins 3.This decomposition is an example of "true" cycloreversion.
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