Monoalkylation of C60 and C70 with Zn and Active Alkyl Bromides

We report a convenient and simple solution-phase electron-transfer reaction of C60 with zinc and α-bromoacetonitrile, α-bromo acetate esters, allyl bromide, benzyl bromide and α-bromo ketones in DMF, with which different types of monoalkylated C60 derivatives can be prepared. When this method is emp...

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Bibliographic Details
Published in:	Journal of organic chemistry Vol. 68; no. 8; pp. 3043 - 3048
Main Authors:	Wang, Zhongwen, Meier, Mark S
Format:	Journal Article
Language:	English
Published:	Washington, DC American Chemical Society 18-04-2003
Subjects:	Cross-disciplinary physics: materials science; rheology Exact sciences and technology Fullerenes and related materials; diamonds, graphite Materials science Physics Specific materials Fullerenes Bromine Organic compounds Carbon molecules NMR spectroscopy Chemical synthesis Alkylation Zinc Atomic clusters Ultraviolet visible spectrometry
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Summary:	We report a convenient and simple solution-phase electron-transfer reaction of C60 with zinc and α-bromoacetonitrile, α-bromo acetate esters, allyl bromide, benzyl bromide and α-bromo ketones in DMF, with which different types of monoalkylated C60 derivatives can be prepared. When this method is employed with C70, 2-carbomethoxymethyl-1,2-dihydro[70]fullerene (isomer 5a) is produced as one of the two 1,2-monoalkylated C70 isomers, together with the first 5,6-monoalkylated C70 derivative.
Bibliography:	istex:9F54B8E4B882F7204163802419E854D2DF86481F ark:/67375/TPS-HC1F7QKL-5 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo020563o