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Preparation and NMR characterization of C70H10: cutting a fullerene pi-system in half

Author
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.

Year of Publication
:
2000
Journal
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The Journal of organic chemistry
Volume
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65
Issue
:
9
Number of Pages
:
2755-8
Date Published
:
2000
ISSN Number
:
0022-3263
DOI
:
10.1021/jo991862p
Short Title
:
J Org Chem
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