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.
Literature cited
C. von Holt, J. Chang, M. von Holt, and H. Bohm, Biochim. Biophys. Acta,90, 611 (1964).
J. A. Carbon, W. B. Martin, and L. R. Swett, J. Am. Chem. Soc.,80, 1002 (1958).
E. F. Ullman and W. J. Fanchane, J. Am. Chem. Soc.,83, 2379 (1961).
D. E. Applequist, M. R. Johnston, and F. Fisher, J. Am. Chem. Soc.,92, 4614 (1970).
I. E. Dolgii, E. A. Shapiro, A. Ya. Shteinshneider, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 2514 (1977).
I. E. Dolgii, E. A. Shapiro, and O. M. Nefedov, Inventor's Certificate 652, 172; Byull. Izobret., No. 10 (1979).
V. I. Kadentsev, A. Ya. Podel'ko, O. S. Chizhov, I. E. Dolgii, E. A. Shapiro, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 2461 (1979).
O. M. Nefedov, I. E. Dolgii, and E. A. Shapiro, Izv. Akad. Nauk SSSR, Ser. Khim., 1209 (1978).
E. A. Shapiro, I. E. Dolgii, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 2096 (1980).
W. R. Mozer, J. Am. Chem. Soc.,91, 1135 (1969).
Ya. M. Slobodin and A. P. Khitrov, Zh. Obshch. Khim.,31, 3945 (1961).
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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