Reactions of C-symmetrical C60 pentakis-adducts with diazomethane: regioselective formation of hexakis- to octakis-adducts and mechanism of methanofullerene formation by addition of diazomethane followed by dinitrogen extrusion

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Richard F. Haldimann, Frank-Gerrit Klärner and François Diederich


Abstract

Repeated treatment of the C-symmetrical C60 pentakis-adducts 1a,b with diazomethane provided with high regioselectively the novel heptakis- 5 and octakis-adducts 4a,b via hexakis-adducts 3a,b; an orbital symmetry-controlled reaction mechanism for the thermal dinitrogen extrusion from the pyrazoline intermediates in the addition of diazomethane to fullerenes is proposed.


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