Relative reactivities of acetals and orthoesters in Lewis acid catalyzed reactions with vinyl ethers. A systematic investigation of the synthetic potential of acetals and …

U Von der Brueggen, R Lammers…

Index: Brueggen, Uwe von der; Lammers, Roswitha; Mayr, Herbert Journal of Organic Chemistry, 1988 , vol. 53, # 13 p. 2920 - 2925

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Citation Number: 21

Abstract

The relative reactivities of acetals and orthoesters in BF3. 0Etz-catalyzed reactions with methyl vinyl ether (-78" C, CH2C12) have been determined by competition experiments. A reactivity increase by 5 orders of magnitude was found in the series: saturated acetals< methyl orthoformate< benzaldehyde acetals< a $-unsaturated acetals; formaldehyde acetals as well as orthoacetates and orthobenzoates did not react under these conditions. The ...