THE REACTIONS OF OLEFINS WITH CHLOROMETHOXYMETHANE OR DIMETHOXYMETHANE IN NITRILES

The Lewis acid-catalyzed reactions of olefins with chloromethoxymethane (CM) or dimethoxymethane (DM) and aliphatic or aromatic nitriles afforded the 1 : 1 : 1 adducts and/or their hydrolysis products in various yields, together with the 1 : 1 olefin–CM (or DM) adducts. AlCl3, FeCl3, ZnCl2, and SnCl4 were effective catalysts for the reaction with CM, whereas BF3 and SnCl4 were effective for that with DM. In the case of cyclohexene, the addition proceeded in the trans-manner; i.e., the methoxymethyl group and the nitrile molecule were added to the olefin from opposite sides.