Mayr, Herbert and Dau-Schmidt, Jan-Peter
Relative Reactivities of Acetals and Ethers under Friedel-Crafts Conditions.
In: Chemische Berichte, Vol. 127, No. 1: pp. 213-217
Competition experiments have been performed to determine the relative reactivities of acetals and ethers toward allyltrimethylsilane in the presence of catalytic amounts of BF3 OEt2. It is found that acetals R-CH(OMe)2 and their phenylogous p-anisyl ethers R-CH(p-MeOC6H4)(OMe) show very little differences in reactivity. The reactivity scales are employed to rationalize the results of Lewis acid-catalyzed additions of acetals and ethers to CC double bonds.