Acrolein acetals as allyl cation precursors in the ionic Diels-Alder reaction

…, DA Singleton, JJ Wilwerding, SP Chavan

Index: Gassman, Paul G.; Singleton, Daniel A.; Wilwerding, James J.; Chavan, Subhash P. Journal of the American Chemical Society, 1987 , vol. 109, # 7 p. 2182 - 2184

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Citation Number: 86

Abstract

H''OR The cycloaddition of la to a series of dienes via the intermediacy of 2a is an attractive reaction because it occurs readily below 0 OC. This can be contrasted with the related Diels- Alder reactions of the intact acetals of a, b-unsaturated ketones and aldehydes, which require long reaction times at high temperature.* As can be noted from Table I, the yields obtained in the addition of 3, 3-diethoxypropene were not attractive from a synthetic point ...