Metal-free-mediated synthesis of fulleropyrrolines by the reaction of [60]fullerene with β-substituted ethylamines

Abstract

The reaction of [60]fullerene with β-substituted ethylamines under air conditions afforded unexpected fulleropyrrolines with trisubstituted alkene functional groups in moderate yields. The conversion of β-substituted ethylamines to their corresponding aldehydes played a crucial role in the successful synthesis of fulleropyrrolines. Promoted by p-toluenesulfonic acid, the obtained fulleropyrroline could (1) be converted back to [60]fullerene in nearly quantitative yield and (2) further react with 1,3-propanediol to generate fullerene-fused dioxepane.