Multiple bond migration with participation of a protophilic agent 3. Double bond migration in 1-methoxy-2-propene molecule with participation of hydroxide ion

The pathways of migration of the double bond in the 1-methoxy-2-propene mol ecule with participation of a hydroxide ion were investigated by the ab ini tio RHF/6-31+G* and MP2/6-31+G* methods. Stationary points corresponding to complexes between the molecule under study and the hydroxide ion and betwe en the corresponding carbanion and a water molecule were found on the poten tial energy surfaces of the proton transfer reactions. As in the propene mo lecule, migration of the double bond in the 1-methoxy-2-propene molecule ca n occur in the gas phase by the mechanism of intramolecular proton transfer involving the proton of the hydroxide ion. Conformational isomerism of the initial molecule and reaction products was considered. The proposed mechan ism of 1,3-hydrogen shift involving the proton-containing base suggests the formation of both E- and Z-products with predominance of the latter irresp ective of the nature of the substituent. In this case the direction of mult iple bond migration will be completely determined by the energy difference between the initial reagents and final products.