C100 is Converted into C94Cl22 by Three Chlorination‐Promoted C2 Losses under Formation and Elimination of Cage Heptagons. Issue 13 (12th February 2015)

• Record Type: Journal Article
• Authors: Ioffe, Ilya N.; Yang, Shangfeng; Wang, Song; Kemnitz, Erhard; Sidorov, Lev N.; Troyanov, Sergey I.
• Is Part Of: Chemistry. Volume 21:Issue 13(2015)
• Page Start: 4904
• Page End: 4907
• Publication Date: 2015-02-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201406487
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Chlorination of the C₁₀₀(18) fullerene with a mixture of VCl₄ and SbCl₅ gives rise to branched skeletal transformations affording non‐classical (<italic>NC</italic>) C₉₄(<italic>NC</italic>1)Cl₂₂ with one heptagon in the carbon cage together with the previously reported C₉₆(<italic>NC</italic>3)Cl₂₀ with three heptagons. The three‐step pathway to C₉₄(<italic>NC</italic>1)Cl₂₂ starts with two successive C₂ losses of 5:6 CC bonds to give two cage heptagons, whereas the third C₂ loss of the 5:5 CC bond from a pentalene fragment eliminates one of the heptagons. Quantum‐chemical calculations demonstrate that the two unusual skeletal transformations—creation of a heptagon in C₉₆(<italic>NC</italic>3)Cl₂₀ through a Stone–Wales rearrangement and the presently reported elimination of a heptagon through C₂ loss—are both characterized by relatively low activation energy.</p> </abstract>