Synthesis of Fullerene-Fused Dioxanes/Dioxepanes: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Diols

J Org Chem. 2015 Jun 19;80(12):6037-43. doi: 10.1021/acs.joc.5b00360. Epub 2015 Jun 2.

Abstract

The facile one-step reaction of [60]fullerene with various diols in the presence of ferric perchlorate afforded a series of rare fullerene-fused dioxanes/dioxepanes. Nevertheless, the reaction of [60]fullerene with diethylene glycol, triethylene glycol, and tripropylene glycol promoted by ferric perchlorate unexpectedly generated fullerene-fused dioxanes instead of the anticipated fullerene-fused crown ethers. A plausible reaction mechanism is proposed to explain the formation of fullerene-fused dioxane/dioxepane products.