Opening and Closure of the Fullerene Cage in cis-Bisimino Adducts of C60: The Influence of the Addition Pattern and the Addend

✍ Scribed by Dipl.-Chem. Georg Schick; Prof. Dr. Andreas Hirsch; Dipl.-Chem. Harald Mauser; Dr. Timothy Clark

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 956 KB
• Volume: 2
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.19960020807

✦ Synopsis

The synthesis, isolation, and spectroscopic characterization of the bisimino[60]fullerenes C,,(NCOOR), (1 a: R = Et, 1 b. R = tBu) with a cis-1 addition pattern as well as of their regioisomeric analogues 2-7 with different addition patterns are described. Whereas compounds 2-7 are typical fulleroaziridines and obey the rule of the minimization of [5,6] double bonds, the cis-1 isomers l a and l b represent the first examples of fullerene derivatives with open transannular [6,6] bonds. Characteristic features within the fullerene framework of these valence isomers VI are the presence of a doubly bridged open 14-membered ring with a phenanthrene perimeter as well as of an 8-membered 1 ,Cdiazocine heterocycle. Moreover, it is shown that, by transforming cis-l-C60(NCOOtBu)2 (1 b) into cis-l-C6O(NH)2 (1 c), the fullerene cage can be closed in an intraring 2 n + 2 c j isomerization to valence isomer V. These are 0