1-3-Dipolar cycloaddition reactions of diazoalkanes. Part III. Substituent effects on the kinetics of reactions between diazomethane and some unsaturated esters

1 January 1967

journal article
research article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic

p. 83-84
https://doi.org/10.1039/j29670000083

Abstract

The kinetics of reactions between diazomethane and several conjugated unsaturated esters have been investigated. Reaction rates are governed by steric effects in a manner very similar to that found by Huisgen for corresponding reactions of diphenyldiazomethane. For the series of esters CH₂:CH·CO·OEt, CH₂:C(CH₃)·CO·OEt, CH₃·CH:CH·CO₂Et, the relative rate coefficients for reaction with diazomethane in tetrahydrofuran fall in the sequence 100 : 6·1 : 0·8, respectively. These observations strongly support a concerted cycloaddition process for the reaction mechanism.

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