Formation of unsaturated bicyclic γ-butyrolactone by oxidative dimerization of 2-methyl-2-ethynylcyclopropanecarboxylic acid |
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Authors: | E. A. Shapiro G. V. Lun'kova A. Ya. Shteinshneider I. E. Dolgii O. M. Nefedov |
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Affiliation: | (1) N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow |
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Abstract: | Conclusions The oxidative dimerization of a mixture of the trans and cis isomers of 2-methyl-2-ethynylcyclopropanecarboxylic acid in the presence of CuCl and NH4Cl gives, along with bis(trans-1-methyl-2-carboxyl-1-cyclopropyl)diacetylene (53% yield), also the corresponding dilactone, and specifically bi(1-methyl-4-oxo-3-oxabicyclo[3.1.0]-2-hexalidene)methyl (14% yield), which is probably formed via the intramolecular cyclization of the intermediately formed bis(cis-1-methyl-2-carboxy-1-cyclopropyl) diacetylene.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1164–1166, May, 1981. |
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