title: Solution-Phase Perfluoroalkylation of C60Leads to Efficient and Selective Synthesis of Bis-Perfluoroalkylated Fullerenes.
abstract: A solution-phase perfluoroalkylation of C60with a series of RFI reagents was studied. The effects of molar ratio of the reagents, reaction time, and presence of copper metal promoter on fullerene conversion and product composition were evaluated. Ten aliphatic and aromatic RFI reagents were investigated (CF3I, C2F5I,n-C3F7I,i-C3F7I,n-C4F9I, (CF3)(C2F5)CFI,n-C8F17I, C6F5CF2I, C6F5I, and 1,3-(CF3)2C6F3I) and eight of them (except for C6F5I and 1,3-(CF3)2C6F3I) were found to add the respective RFgroups to C60in solution. Efficient and selective synthesis of C60(RF)2derivatives was developed.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
authors.forename: Igor V
authors.initials: IV
authors.lastname: Kuvychko
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
authors.forename: Steven H
authors.initials: SH
authors.lastname: Strauss
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
authors.forename: Olga V
authors.initials: OV
authors.lastname: Boltalina
keywords: C60; RFI; fullerene; perfluoroalkyl radicals; perfluoroalkylation
references.citation: Chemistry. 2008;14(1):107-21
references.pmid: 17972264
references.citation: Angew Chem Int Ed Engl. 2008;47(33):6204-7
references.pmid: 18618569
references.citation: J Am Chem Soc. 2008 Oct 8;130(40):13471-89
references.pmid: 18788799
references.citation: Chemistry. 2009 Oct 12;15(40):10486-92
references.pmid: 19739224
references.citation: Chemistry. 2010 Apr 26;16(16):4721-4
references.pmid: 20349474
references.citation: Science. 1993 Oct 15;262(5132):404-7
references.pmid: 17789947
references.citation: Chem Rev. 1996 Aug 1;96(5):1557-1584
references.pmid: 11848804
references.citation: J Am Chem Soc. 2005 Jun 15;127(23):8362-75
references.pmid: 15941270
references.citation: Chem Commun (Camb). 2011 Jan 21;47(3):875-7
references.pmid: 21063613
references.citation: Inorg Chem. 2011 Apr 18;50(8):3766-71
references.pmid: 21417230
references.citation: J Org Chem. 2009 Sep 4;74(17):6902-5
references.pmid: 19663505
references.citation: J Am Chem Soc. 2010 May 12;132(18):6443-62
references.pmid: 20408522
references.citation: J Org Chem. 1997 Oct 17;62(21):7128-7136
references.pmid: 11671816
references.citation: J Am Chem Soc. 2007 Sep 19;129(37):11551-68
references.pmid: 17718489
references.citation: Chem Commun (Camb). 2006 Jan 21;(3):308-10
references.pmid: 16391743
references.citation: J Am Chem Soc. 2011 Mar 2;133(8):2672-90
references.pmid: 21294511
references.citation: Org Lett. 2011 May 20;13(10 ):2548-51
references.pmid: 21513298
references.citation: Angew Chem Int Ed Engl. 2005 Mar 11;44(12):1846-9
references.pmid: 15719350
references.citation: Org Lett. 2010 May 21;12 (10 ):2374-7
references.pmid: 20411917
references.citation: Angew Chem Int Ed Engl. 2009;48(48):9102-4
references.pmid: 19894240
references.citation: Chemistry. 2010 May 10;16(18):5343-53
references.pmid: 20209515
references.citation: Chemistry. 2006 May 3;12(14):3876-89
references.pmid: 16550623
references.citation: J Am Chem Soc. 2006 Sep 20;128(37):12268-80
references.pmid: 16967978
references.citation: Chem Rev. 2011 Aug 10;111(8):4475-521
references.pmid: 21456523