Abstract
Reductive cyclization of 4-hydroxymethyl-5,5-dimethyl(or pentamethylene)-2,5-dihydrofuran-2-ones by the action of sodium tetrahydridoborate gave bicyclic compounds in which the lactone ring is fused to a cyclopropane ring. Hydrolysis of the products with aqueous sodium hydroxide resulted in the formation of the corresponding disodium cyclopropane-1,1-dicarboxylates, which reacted with alkyl halides to produce the diesters. Acid hydrolysis of the fused systems was accompanied by opening of the cyclopropane ring with formation of 4-chloromethyl-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylic acid.
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Avetisyan, A.A., Tokmadzhyan, G.G., and Karapetyan, L.V., Uch. Zap. Erev. Gos. Univ., 2003, no. 1, p. 80.
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Original Russian Text © A.A. Avetisyan, G.G. Tokmadzhyan, L.V. Karapetyan, L.S. Balayan, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 12, pp. 1822–1825.
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Avetisyan, A.A., Tokmadzhyan, G.G., Karapetyan, L.V. et al. Synthesis and some transformations of bicyclic γ-lactones with a fused cyclopropane ring. Russ J Org Chem 44, 1795–1798 (2008). https://doi.org/10.1134/S1070428008120129
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DOI: https://doi.org/10.1134/S1070428008120129