Synthesis of several pyrrolidinofullerenes containing structural units of natural amino acids

Pavel A. Troshin, Rimma N. Lyubovskaya

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

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 [60]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.

Original languageEnglish
Pages (from-to)345-351
Number of pages7
JournalFullerenes Nanotubes and Carbon Nanostructures
Volume13
Issue number4
DOIs
Publication statusPublished - Oct 2005
Externally publishedYes

Keywords

  • [2 + 3]cycloaddition
  • Azomethine ylides
  • C
  • Fullerene

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