Diels-Alder reactions of the [60]fullerene functionalizing a carbon sphere with flexibly and with rigidly bound addends

Organofullerene Materials

“…By using an excess of fullerene the amount of multiadducts is minimized, while by using an excess of diene the formation of such multiadducts can be increased. In fact, the latter has been described by the synthesis of a hexakis adduct of organofullerene, upon cycloaddition of 2,3-dimethyl-1,3-butadiene to C 60 [106,107].…”

Cycloadditions

“…The corresponding [5,6] bridged isomer is -if at all -formed only in small amounts, probably via a direct addition to the [5,6] bond [394]. Nitrenes have been generated by thermolysis of azido-formic esters [172,[395][396][397][398][399][400], photolysis of aroyl azides [401] or aryl azide [402], elimination of O-4-nitrophenylsulfonylalkylhydroxamic acid [403] or reaction of amines with Pb(OAc) 4 [404].…”

Decomposition of the electronic activity in competing [5,6] and [6,6] cycloaddition reactions between C60 and cyclopentadiene

“…Moreover, C 60 reacts through many metal-catalysed processes like the Pauson-Khand reactions [7][8][9], the Suzuki-Miyaura reactions [10][11][12][13] or the [2 + 2 + 2] cycloadditions [14][15][16], among others. However, one of the most employed reactions for the functionalization of fullerenes and their derivatives is the Diels-Alder (DA) cycloaddition [17][18][19][20][21][22]. The electronwithdrawing nature of C 60 makes this molecule an ideal dienophile for DA reactions [23].…”