Chapter

The reactivity of the 5,6 -bond in cycloadditions to fullerenes

ISBN: 1-56677-317-2 pp.244-269

ABSTRACT The synthesis of [5,6]-regioisomers in the field of fullerene chemistry has proven to be difficult given that direct additions to the [5,6]-ring junctions in fullerenes are uncommon. In this work we analyze theoretically the reactivity of the [5,6]- as compared to the [6,6]-bonds in fullerenes for different cycloaddition reactions including Diels-Alder cycloadditions, 1,3-dipolar cycloadditions, and [1+2] nitrene additions. The reasons for the usually low reactivity of the [5,6]-bond in fullerenes are discussed.

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Keywords

1,3-dipolar cycloadditions
 
[1+2] nitrene additions
 
Diels-Alder cycloadditions
 
different cycloaddition reactions
 
direct additions
 
fullerenes
 
theoretically