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Synthesis of 2-chloroethyl diazoacetate and study of its carbenic decomposition

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    2-Chloroethyl diazoacetate was obtained in an overall yield of 75% by esterification of glycine with ethylene chlorohydrin by the action of gaseous HCl, followed by diazotization of the 2-chloroethyl aminoacetate formed.

  2. 2.

    Thermal and thermocatalytic decomposition of 2-chloroethyl diazoacetate at > 80°C is carbenic in character and in the presence of olefinic and acetylenic acceptors of m-xylene leads with preparative yields to 2-chloroethyl esters of cyclopropanecarboxylic, cyclopropenecarboxylic, and cycloheptatrienecarboxylic acids, respectively.

  3. 3.

    Thermal decomposition of 2-chloroethyl diazoacetate in the presence of diglyme is accompanied by splitting of the ether bonds with the formation of 2-chloroethyl esters of alkoxyacetic acids in a 24% yield. Under the same conditions, the reaction of this diazoester with ethylene glycol monomethyl ether leads to 2-chloroethyl ester of 2-methoxyethoxyacetic acid (in a 25% yield), the product of formal introduction of 2-chloroethoxycarbonylcarbene at the O-H bond.

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Literature cited

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    E. A. Shapiro, G. V. Lun'kova, I. E. Dol'gii & O. M. Nefedov

Authors
  1. E. A. Shapiro
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  2. G. V. Lun'kova
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  3. I. E. Dol'gii
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  4. O. M. Nefedov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2529–2535, November, 1984.

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Shapiro, E.A., Lun'kova, G.V., Dol'gii, I.E. et al. Synthesis of 2-chloroethyl diazoacetate and study of its carbenic decomposition. Russ Chem Bull 33, 2317–2322 (1984). https://doi.org/10.1007/BF00948845

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  • DOI: https://doi.org/10.1007/BF00948845

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