The paper reports on the investigation of reactivity of various imines prepared from esters of alanine, phenylalanine and tyrosine, and various aromatic aldehydes in reactions with fullerene. Almost all imines studied were found not to undergo [2 + 3]cycloaddition reactions with C60 under continuous reflux in 1,2-dichlorobenzene because of steric hindrances of the substrates. However, imines of pyridine-2-carboxaldehyde readily reacted with C60 to form corresponding pyrrolidino-fullerenes with moderate yields. The promoting effect of 2-pyridyl group in the [2 + 3] cycloaddition reactions was observed as a result of the formation of intramolecular hydrogen bonds in azomethine ylides formed.
- [2 + 3]cycloaddition
- Azomethine ylides