A NOVEL HETEROCYCLE-STABILIZED ALLYLIC ANION ROUTE TO CYCLOPROPANES, 1-ETHOXY-1-VINYLETHYLENE OXIDES, 1-HYDROXYALKYL 2-METHOXYETHYL KETONES, 1-HYDROXYALKYL VINYL KETONES, BETA-ETHOXY-BETA-VINYLALKYL ALCOHOLS, GAMMA-LACTONES, AND BETA,GAMMA-UNSATURATED CARBOXYLIC-ACIDS

Treatment of N-(alpha-ethoxyallyl)benzotriazole (8) with butyllithium followed by alpha,beta-unsaturated esters at -78 degrees C formed the 1,1-adducts 11 which underwent internal displacement of the benzotriazolyl group at 20 degrees C to give cyclopropanecarboxylic esters 14 and 15. In the presence of ZnBr2, addition of anion 13 to cyclic and methyl ketones gave 1-ethoxy-1-vinylethylene oxides 25 in good yields. Epoxides 25 were subsequently converted to 1-hydroxyalkyl 2-methoxyethyl ketones 24, 1-hydroxyalkyl vinyl ketones 26, and beta-ethoxy-beta-vinylalkyl alcohols 27. Treatment of anion 13 with aromatic ketones or sterically hindered aliphatic ketones produced gamma-alkylated adducts 31 which were hydrolyzed to beta,gamma-unsaturated carboxylic acids 32 (R(1), R(2) = aromatic) or gamma-lactones 33 (R(1), R(2) = aliphatic).