Regioselective Addition of Butenyl Grignard Reagent to the Unactivated Double Bond of 2-(α-Methylallyl) Aza Aromatic Compounds

Article abstract of DOI:10.1021/jo00354a019

The addition of the butenyl Grignard reagent to the unactivated double bond of 2-(α-methylallylic) aza aromatic compounds is completely regioselective giving the 2-(1,4-dimethyl-5 hexen-1-yl) aza aromatics in good yield.A preliminary coordination of magnesium atom to nitrogen atom and the formation of a six-center transition state involving the butenyl Grignard and the vinyl group has been proposed in order to explain the selectivity of the reaction.