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Manganese(III) acetate-mediated radical reaction of [60]fullerene with bromoacetic acid, 3-chloropropionic acid or 1-naphthylacetic acid

  • Article
  • Organic Chemistry
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Chinese Science Bulletin

Abstract

The manganese(III) acetate-mediated radical reaction of [60]fullerene (C60) with three carboxylic acids, that is, bromoacetic acid, 3-chloropropionic acid, and 1-naphthylacetic acid, was investigated. The reaction of C60 with bromoacetic acid in the presence of 4-(dimethylamino)pyridine afforded the anticipated C60-fused lactone, while the reaction with 3-chloropropionic acid unexpectedly led to the formation of a novel C60-fused lactone with the loss of one molecule of HCl. Interestingly, the reaction with 1-naphthylacetic acid under similar conditions gave both C60-fused lactone and 1,4-adduct, yet each of them could be selectively obtained by controlling reaction conditions. It was also observed that the C60-fused lactone bearing a bulky naphthyl group existed as two isomers.

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Authors and Affiliations

  1. Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China

    FaBao Li, SanE Zhu & GuanWu Wang

  2. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, China

    GuanWu Wang

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  1. FaBao Li
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  2. SanE Zhu
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  3. GuanWu Wang
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Correspondence to GuanWu Wang.

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Li, F., Zhu, S. & Wang, G. Manganese(III) acetate-mediated radical reaction of [60]fullerene with bromoacetic acid, 3-chloropropionic acid or 1-naphthylacetic acid. Chin. Sci. Bull. 55, 2909–2914 (2010). https://doi.org/10.1007/s11434-010-4016-4

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  • DOI: https://doi.org/10.1007/s11434-010-4016-4

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