Preparation and NMR characterization of C70H10: Cutting a fullerene π-system in half

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Abstract

Three isomers of C70H10 were prepared by Zn(Cu) reduction of C70. Three chromatographic bands were identified as C70H10 species by MALDI-FT mass spectrometry, and these compounds were isolated by repeated HPLC treatments. The major isomer (2) was characterized by 1H and 13C NMR, while the minor isomers 3-4 were isolated in such small quantities that only 1H NMR analysis was possible. 1H-coupled and 1H-decoupled 13C NMR of 2 established a 7,8,19,26,33,37,-45,49,53,63-substitution pattern. This assignment was confirmed by HMBC and DFQ-COSY experiments. This structure is completely reasonable, as we found that 2 results exclusively from reduction of the 7,19,23,27,33,37,44,53-C70H8 that is formed in the course of the Zn(Cu) reduction of C70.

Original languageEnglish
Pages (from-to)2755-2758
Number of pages4
JournalJournal of Organic Chemistry
Volume65
Issue number9
DOIs
StatePublished - May 5 2000

ASJC Scopus subject areas

  • Organic Chemistry

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