The gas-phase elimination reaction of 3-methoxycyclohexene: Regiochemistry

Article abstract of DOI:10.1016/S0040-4039(00)79867-4

Gas-phase elimination reactions of deuterium labeled 3-methoxycyclohexenes have been investigated. 1,4-Elimination is heavily favored over 1,2-elimination when strong bases such as hydroxide and amide are used. The 1,2-pathway becomes more competitive when weaker bases such as methoxide are employed, and the mechanism shifts from E1 cB to E2.