University of Sussex
Browse

File(s) not publicly available

In the first proven S(N)2 ' fullerene reaction, both C-3 and C1 C60F36 hydrolyse to C-1 isomers of C60F35OH that eliminate HF to give epoxides C60F34O; C60F36O oxides are shown to be ethers, and a fourth isomer of C60F36 exists

journal contribution
posted on 2023-06-07, 20:36 authored by Anthony G Avent, Ala'a K Abdul-Sada, Brian W Clare, David L Kepert, Joan M Street, Roger Taylor
On standing in organic solvents containing traces of water, C-3 and C-1 isomers of C60F36 slowly convert to C-1 isomers of C60F35OH. Both fluorofullerenols eliminate HF during EI mass spectrometry to give C60F34O epoxides, one fullerenol being much less stable than the other to the extent that the mass spectrum shows only the epoxide. Both C60F35OH isomers have C-1 symmetry, one being identified by the remarkable linear relationship between chemical shifts in its F-19 NMR spectrum and those in the spectrum of C1C60F36; the spectrum of the other shows the pattern of C3C60F36 rendered asymmetrical by the replacement of one F by OH. The reactions are facilitated by the presence of isolated double bonds, and provide the first proven examples of an S(N)2' reaction of a fullerene derivative. Our observation explains why only a limited number of fluorines are readily replaced in C60F36 and why C60F18 is by contrast much more resistant to hydrolysis. We have isolated also a pure isomer of C60F36O, which is shown to be an oxahomofullerene (ether) apparently derived from C1C60F36, and an impure fraction comprising a fourth isomer of C60F36, a trifluoromethyl derivative of C60F36, a second isomer of C60F36O, and an unknown species of 1392 u.

History

Publication status

  • Published

Journal

Organic and Biomolecular Chemistry

ISSN

1477-0520

Publisher

Royal Society of Chemistry

Issue

6

Volume

1

Page range

1026-1033

Pages

8.0

Department affiliated with

  • Chemistry Publications

Notes

AAS carried out the advanced analytical chemistry and mass spectroscopy necessary for this publication and co-authored the manuscript in collaboration with the late RT

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-02-06

Usage metrics

    University of Sussex (Publications)

    Categories

    No categories selected

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC