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Simple synthesis of esters of methylenecyclopropanecarboxylic acid from alkyl diazoacetates and allene gas

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

The thermal and thermocatalytic reaction of alkyl diazoacetates with allene gas at 125–280° in a reactor of the flow type proceeds to give the esters of methylenecyclopropanecarboxylic acid in up to 50% yield, whose saponification with aqueous alcoholic alkali solution gives 2-methylenecyclopropanecarboxylic acid in up to 80% yield.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2405–2408, October, 1983.

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Dolgii, I.E., Shapiro, E.A. & Nefedov, O.M. Simple synthesis of esters of methylenecyclopropanecarboxylic acid from alkyl diazoacetates and allene gas. Russ Chem Bull 32, 2168–2170 (1983). https://doi.org/10.1007/BF00955800

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  • DOI: https://doi.org/10.1007/BF00955800

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