Reaction of cyclopropenone ketals with alcohols

GB Butler, KH Herring, PL Lewis…

Index: Butler,G.B. et al. Journal of Organic Chemistry, 1977 , vol. 42, p. 679 - 682

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Citation Number: 17

Abstract

3, 3-Dimethoxycyclopropene (I), synthesized as previously described, undergoes a ring- opening reaction under mild conditions, with a variety of alcohols to give the corresponding monoalkyl dimethyl orthoacrylates. These results are consistent with a mechanism which involves initial protonation of 1 followed by solvolysis of the intermediate allyl oxonium cation. Less mild conditions result in exchange reactions between the alcohol and the ...