Cycloaddition Reactions: Reaction of 3-Methyl-2-phenylpyrrocoline with Dimethyl Acteylenedicarboxylate

Reaction of 3-methyl-2-phenylpyrrocoline(I) and dimethyl acetylenedicarboxylate(II) in refluxing toluene furnishes cis-7',8-dihydro.4,5,8,9-tetramethoxycarbonyl-7'-phenyl-7' -methylazocino(2,1,8-cd]pyrrolizine (III) and trans-7',8-dihydro-4,5,8,9-tetramethoxycarbonyl-7-phenyl-7'-methylazocino[2,1,8-cd]pyrrolizine (IV), while the same reaction at ambient temperature yields 1-[(1,2-trans-dimethoxycarbonyl)vinyl]-3-methyl-2-phenylpyrrocoline (V) and 1-[(1,2-cis-di(methoxycarbonyl)vinyl)--methyl-2- phenylpyirocoUne (V) and 1-[(I,2-cis-di(methoxycarbonyl)Yinyl]-3-metbyl-2-phenylpyrrocoline(VI) as the major products. The structure of IV has been determined by X-ray crystallography.A possible mechanism of formation of these products is also discussed.