F. V. D. Maeden, H. Steinberg, T. Boer
1972
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Influential Citations
2
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
In aqueous sodium hydroxide, cyclopropanecarbaldehyde 1 disproportionates exclusively into cyclopropylmethanol 2 and cyclopropanecarboxylic acid 3 (Cannizzaro reaction). The reaction is second order in aldehyde and second order in base and shows a small positive salt effect. These results and the absence of deuterium incorporation in the alcohol 2, when the reaction is carried out in D2O, have been rationalized in scheme 1. The enthalpy and entropy of activation are found to be ΔH≠ = 11.7 ± 0.6 kcal/mole and ΔS≠ = −17.5 ± 1.0 e.u. (74°). The results of the crossed Cannizzaro reaction between benzaldehyde and cyclopropanecarbaldehyde suggests that cyclopropyl is a better electron-donating group than phenyl.