Reactions of [60]Fullerene with Acetone under Basic Condition: Nucleophilic Ring Opening of the [5,6]-Cyclopropane in C60 and Formation of the Substituted Methano[60]Fulleroids

Si Chen; Wei-Wei Yang; Hui-Lei Hou; Zong-Jun Li; Xiang Gao

doi:10.1021/acs.joc.0c02902

Reactions of [60]Fullerene with Acetone under Basic Condition: Nucleophilic Ring Opening of the [5,6]-Cyclopropane in C₆₀ and Formation of the Substituted Methano[60]Fulleroids

J Org Chem. 2021 Mar 19;86(6):4843-4848. doi: 10.1021/acs.joc.0c02902. Epub 2021 Feb 25.

Authors

Si Chen¹, Wei-Wei Yang², Hui-Lei Hou², Zong-Jun Li², Xiang Gao²

Affiliations

¹ College of Chemistry and Chemical Engineering, Yantai University, 30 Qingquan Road, Yantai, Shandong 264005, China.
² State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022, China.

PMID: 33630594
DOI: 10.1021/acs.joc.0c02902

Abstract

The reactions of C₆₀ with acetone were carried out under basic condition in the presence of 1.0 M TBAOH (tetra-n-butylammonium hydroxide) methanol solution and ArCH₂Br (Ar = Ph or o-BrPh), where methano[60]fulleroids with a novel 1,1,4,9,9,25-configuration were obtained and structurally characterized by single crystal diffraction. The product was formed via the ring-opening reaction of the [5,6]-cyclopropane by the nucleophilic addition of MeO^-, which is different from the reactions of other ketones reported previously.