Amination of [60]fullerene by ammonia and by primary and secondary aliphatic amines - Preparation of amino[60]fullerene peroxides

Xiangqing Hu, Zhongping Jiang, Zhenshan Jia, Shaohua Huang, Xiaobing Yang, Yuliang Li, Liangbing Gan, Shiwei Zhang, Daoben Zhu

Research output: Contribution to journalArticle

25 Scopus citations

Abstract

Ammonia and aliphatic amines react readily in the oxygen-rich regions of the Cs symmetric fullerene peroxides C60(O)(OOtBu) 4 (1) and C60(OH)(Br)(OOtBu)4 (2c). Michael addition-type hydroamination of the 1,4-diene moiety on the central skewpentagon was observed when 1 was treated with ammonia or with nonbulky primary amines, while sterically demanding primary amines opened the epoxy moiety to form vicinal aminohydroxy fullerene compounds with the amino group on the central pentagon. In 2c the bromo group was replaced under similar conditions by ammonia and primary amines. Cyclic secondary amines showed different reaction patterns, forming hydrogenation products or aminoketal-fullerenes when treated with 1 and 2c, respectively. Single-electron transfer (SET) is the key step in all the proposed mechanisms. The compounds were characterized by their spectroscopic data, and in addition, three single-crystal X-ray structures were obtained.

Original languageEnglish (US)
Pages (from-to)1129-1141
Number of pages13
JournalChemistry - A European Journal
Volume13
Issue number4
DOIs
StatePublished - 2007

Keywords

  • Amines
  • Fullerenes
  • Peroxides
  • Radicals
  • Single-electron transfer

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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