Studies of the reactions of the anhydrosulphites of α-hydroxy-carboxylic acids. Part IV. Steric and electronic effects in the reaction with alcohols
- 1 January 1970
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 1044-1048
- https://doi.org/10.1039/j29700001044
Abstract
Factors affecting the rate of reaction of anhydrosulphites with alcohols have been studied. The nature of the C(5) substituent in the anhydrosulphite ring has been shown to exert a marked influence on the susceptibility of the C(4) carbonyl group to nucleophilic attack. The effect is attributed to changes in electron density consequent upon the electron-withdrawing, or -donating, power of the C(5) substituent. Variations in the structure of the attacking alcohol have been studied and shown to exert a less marked influence on the reaction. The relevance of these results to the effect of anhydrosulphite structure on its polymerisability is discussed.Keywords
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