E. Shapiro, M. Protopopova, O. M. Nefedov
Oct 1, 1988
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Journal
Bulletin of the Academy of Sciences of the USSR, Division of chemical science
Abstract
Conclusions1.Methyl 1-alkylcycloprop-3-enoates have been shown to add phenol and 4-nitrophenol in the presence of 5–100 mole% of CuCl·2MeC≡CSiMe3 at the C2-C3 bond with opening of the three-membered ring and the formation of 30–80% of the corresponding methyl Z- and E-4-phenoxy-3-alkylbut-3-enoates.2.2,4-Dinitrophenol, butyl mercaptan, and 4-methylcyclohex-4-ene-1,2-dicarboximide on reaction with methyl 1-methylcyclopropene-3-carboxylate in the presence of 20–100 mole% of CuCl·2MeC≡CSiMe3 do not give addition products, functioning merely as proton donors to give the methyl Z- and E-4-chloro-3-methylbut-3-enoates in yields of up to 60%.