An alternative type of fullerene products from the reaction of [60]fullerene with alkoxides and subsequent derivatization

Guan-Wu Wang; Yong-Ming Lu; Zhong-Xiu Chen; Shi-Hui Wu

doi:10.1021/jo9005848

An alternative type of fullerene products from the reaction of [60]fullerene with alkoxides and subsequent derivatization

J Org Chem. 2009 Jul 3;74(13):4841-8. doi: 10.1021/jo9005848.

Authors

Guan-Wu Wang¹, Yong-Ming Lu, Zhong-Xiu Chen, Shi-Hui Wu

Affiliation

¹ Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, People's Republic of China. gwang@ustc.edu.cn

PMID: 19505103
DOI: 10.1021/jo9005848

Abstract

Reaction of [60]fullerene with freshly prepared RCH(2)CH(2)ONa/RCH(2)CH(2)OH (R = H, Me, Et, Ph) in anhydrous toluene in the presence of air unexpectedly afforded fullerene products with a C(60)-fused tetrahydrofuran ring skeleton and an acetal moiety, which could be further transformed into C(60)-fused dihydrofurans, tolyl-substituted C(60)-fused tetrahydrofuran, and methanofullerenes bearing a formyl group by boron trifluoride etherate. Possible reaction mechanisms are proposed to explain the formation of different fullerene products.