Conclusions
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1.
A new preparative method has been developed for the synthesis of 2-bromoethyl diazoacetate by esterification of glycine with ethylene glycol by the action of HBr, with simultaneous substitution of the OH group by the Br atom, followed by diazotization of 2-bromoethyl aminoacetate formed.
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2.
The thermocatalytic decomposition of 2-bromoethyl diazoacetate in the presence of Rh(OAc)2 and powdered copper is carbenic in character, and in the presence of olefinic and acetylenic acceptors it leads to a 2-bromoethyl esters of cyclopropanecarboxylic or cyclopropenecarboxylic acids in 50–65% yields.
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E. A. Shapiro, G. V. Lun'kova, I. E. Dolgii, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 2629 (1984).
J. Frank and R. Schwyter, Experientia,26, 1207 (1970).
E. A. Shapiro, G. V. Lun'kova, I. E. Dolgii, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 1316 (1981).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2535–2540, November, 1984.
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Shapiro, E.A., Romanova, T.N., Dolgii, I.E. et al. Synthesis and carbenic decomposition of 2-bromoethyl diazoacetate. Russ Chem Bull 33, 2323–2327 (1984). https://doi.org/10.1007/BF00948846
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DOI: https://doi.org/10.1007/BF00948846