Methoxylation of Singly Bonded 1,4-1',4'-BnC60-C60Bn Dimer: Preferential Formation of 1,4-C60 Adduct with Sterically Less Demanding Addends and Stability Difference between 1,2- and 1,4-OMe(Bn)C60

Fa-Gui He; Zong-Jun Li; Xiang Gao

doi:10.1021/acs.joc.6b01171

Methoxylation of Singly Bonded 1,4-1',4'-BnC60-C60Bn Dimer: Preferential Formation of 1,4-C60 Adduct with Sterically Less Demanding Addends and Stability Difference between 1,2- and 1,4-OMe(Bn)C60

J Org Chem. 2016 Aug 5;81(15):6838-42. doi: 10.1021/acs.joc.6b01171. Epub 2016 Jul 20.

Authors

Fa-Gui He¹, Zong-Jun Li¹, Xiang Gao¹

Affiliation

¹ State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 5625 Renmin Street, Changchun, Jilin 130022, China.

PMID: 27387300
DOI: 10.1021/acs.joc.6b01171

Abstract

Methoxylation of the singly bonded 1,4-1',4'-BnC60-C60Bn dimer afforded 1,4-OMe(Bn)C60, a 1,4-C60 adduct with sterically less demanding addends, as the major adduct. The situation was different from that of direct functionalization of C60, where 1,2-OMe(Bn)C60 was obtained as the major product. The reaction was studied with in situ vis-NIR spectroscopy and computational calculations to obtain a better understanding of this unusual regioselectivity. The stability difference between 1,2- and 1,4-OMe(Bn)C60 was studied.

Publication types

Research Support, Non-U.S. Gov't