Synthesis of chlorinated fullerenes C60Cln (n = 2, 4) from C60Cl6 and their Arbuzov-type reaction with P(OEt)3. Issue 7 (14th February 2018)

• Record Type: Journal Article
• Authors: Zhilenkov, Alexander V.; Peregudov, Alexander S.; Chernyak, Alexander V.; Martynenko, Vyacheslav M.; Troshin, Pavel A.
• Is Part Of: Tetrahedron letters. Volume 59:Issue 7(2018)
• Page Start: 608
• Page End: 611
• Publication Date: 2018-02-14
• Subjects: Low-chlorinated fullerenes -- Phosphites -- Arbuzov-type reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.11.047
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Reduction of C60 Cl6 with PPh3 produces the lowest chlorinated fullerenes C60 Cln (n = 2–4) Chlorofullerene 1, 4-C60 Cl2 was isolated and characterized for the first time. A mixture of C60 Cl2-4 was successfully used for the preparation of C60 [P(O)(OR)2 ]3 H. Abstract: Reduction of C60 Cl6 with triphenylphosphine was demonstrated to be a useful method for the preparation of a mixture of low-chlorinated fullerenes C60 Cln (n = 2, 4). Individual chlorofullerene 1, 4-C60 Cl2 was isolated by preparative gel permeation chromatography and characterized spectroscopically for the first time. The Arbuzov-type reaction of C60 Cln with P(OEt)3 produced C60 [PO(OEt)2 ]3 H as a major isolable product, which was further hydrolyzed to C60 [PO(OH)2 ]3 H.