Diels-Alder versus 1,3-dipolar cycloaddition pathways in the reaction of C20 fullerene and 2-furan nitrile oxide

Abstract

As one of the smallest carbon cages, C20 and its properties are very important. The nature of these compounds, and the development of procedures for their functionalisation for end-use in nano sized devices, have become important fields. Both Diels–Alder and 1,3-dipolar cycloaddition reactions are appropriate strategies to functionalise carbon nano tubes and C60 fullerenes. In this regard a comparison between two pathways of interaction between C20 and 2-furan nitrile oxide has been performed here to determine which reaction, Diels–Alder or 1,3-dipolar addition, is more suitable for functionalisation of C20. The results showed that 1,3-dipolar cycloaddition is faster than the Diels–Alder reaction for the functionalisation of C20 fullerene by 2-furan nitrile oxide.