Computed Properties of C10H16O4《The preparation of ethyl 1,1-cyclobutanedicarboxylate》 was published in 1953. The authors were Raik, S. E.;Kazanskii, B. A., and the article was included in《Vestnik Moskovskogo Universiteta》. The author mentioned the following in the article:
During the condensation of CHNa(CO2Et)2 (I) with Br(CH2)3Cl a reversible side reaction between I and Cl(CH2)3CNa(CO2Et)2 (II) is known to take place. II was prevented from separating out and the yield of di-Et 1,1-cyclobutanedicarboxylate was increased to 60% (from 35 to 40%, cf. C.A. 37, 4705.6) by employing a mixture of C6H6 and EtOH as solvent. I is only slightly soluble in cold C6H6 but its solubility increases with higher temperature, and particularly in the presence of CH2(CO2Et)2, thus controlling the rate of reaction. Cf. Sidgwick and Brewer, C.A. 20, 740. PrOH and iso-PrOH were unsuccessful in replacing EtOH. To complete the study, the researchers used Diethyl cyclobutane-1,1-dicarboxylate (cas: 3779-29-1) .
Diethyl 1,1-cyclobutanedicarboxylate(cas:3779-29-1 Computed Properties of C10H16O4) reacts with silicon to form diethyl esters and magnesium to form magnesium salts. The reaction time for this compound is short, which may be due to its ability to undergo debromination.
Reference:
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