Reactions of anionic oxygen nucleophiles with C60 revisited

Wei-Wei Chang; Zong-Jun Li; Wei-Wei Yang; Xiang Gao

doi:10.1021/ol300805p

Reactions of anionic oxygen nucleophiles with C60 revisited

Org Lett. 2012 May 4;14(9):2386-9. doi: 10.1021/ol300805p. Epub 2012 Apr 19.

Authors

Wei-Wei Chang¹, Zong-Jun Li, Wei-Wei Yang, Xiang Gao

Affiliation

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

PMID: 22515146
DOI: 10.1021/ol300805p

Abstract

Reactions of C(60) with oxygen nucleophiles of HO(-) and CH(3)O(-) are revisited in PhCN in the presence of PhCH(2)Br. Different from previous results that such reactions lead to the formation of complex mixtures, well-structured C(60) oxazolines are obtained when HO(-) is involved, while di- and tetraadducts with methoxy and benzyl addends are obtained when CH(3)O(-) is engaged. The reactions are followed by in situ vis-near-IR spectroscopy, which reveals further information for the reactions.