Regioselective Thermal Reaction between Triethylamine and C₆₀ Revisited: X‐ray Confirmation of the Pentane‐Fused Adduct and in Situ Mechanism Study

Abstract

We have made a systematic investigation of the regioselective reaction between triethylamine and C 60 under thermal conditions, presenting X-ray crystallographic results of the pentane-fused adduct for the first time. In addition to finding

Multicomponent Synthesis of 2‐Arylvinyl‐Substituted Fulleropyrrolidines from [60]Fullerene, Amines and Aldehydes

“…On the basis of the above results and previous literature,[10h], , , , plausible mechanisms leading to the formation of fulleropyrrolidines 5 are depicted in Scheme and Scheme . Firstly, Et 3 N transfers an electron to C 60 to generate cationic radical Et 3 N · + and anion radical C 60 · – under high‐temperature conditions.…”

“…We have investigated the thermal reactions between C 60 and tertiary amines, and also reactions of C 60 with tertiary amines and aldehydes, both affording cyclopentafullerene derivatives with high stereoselectivity . More recently, the Lu group revisited the regioselective thermal reaction between C 60 and triethylamine . In continuation of our interest in fullerene chemistry,[8c], [10b], [10f], [10h], , , herein we report the facile synthesis of 2‐arylvinyl‐substituted fulleropyrrolidines with high stereoselectivity by three types of multicomponent reactions of C 60 .…”

Copper-Catalyzed Reaction of C60 with Tertiary Amines for the Preparation of Spiro-Linked Methanofullerenes and Fullerenoalkanals

“…To the best of our knowledge, this is perhaps the simplest and most convenient method to access these two kinds of organofullerenes. It is in sharp contrast to the previously reported photoreactions or thermal reactions of C 60 , which afford the fulleropyrrolidines or cyclopentane-fused fullerene derivatives . The abundance of commercially available tertiary amines further shows the practical synthetic value of this approach.…”

Diameter-Selective Host-Guest Interactions between Functionalized Fullerenes and Single-Walled Carbon Nanotubes

“…The RBM Peaks (cm The UV-Vis-NIR spectroscopic results for the empty SWCNTs, C60@SWC 1@SWCNTs, 2@SWCNTs, and 3@SWCNTs, together with the corresponding precu (C60, 1, 2 and 3), are shown in Figure 4 (Figures S8 and S10-S12), to allow further in gation of the inner-outer interactions. The precursors (C60, 1, 2 and 3) dissolved display strong bands at around 330 nm, with a characteristic absorption peak at abo nm for the [6,6]-addition patterns in 1, 2 and 3 [13,31]. However, these characteristic disappear completely after encapsulation inside nanotubes, indicating a shielding of the π-system of SWCNTs on the absorption of fullerene derivatives.…”

“…The fullerene derivative 1 C 60 (C 6 H 15 N) (Figures S2 and S3) was synthesized according to a previously reported procedure [31]; the fullerene derivative 2 C 60 (C 12 H 14 O 2 ), PC 61 BM (>99.5%, HPLC) was purchased from Luminescence Technology Corp; the fullerene derivative 3 C 60 (C 17 H 27 NO) was prepared according to the procedure outlined in Scheme 1.…”