The reaction is of importance in the field of chemistry because it allows the introduction of useful extensions to the fullerene sphere. These extensions alter their properties, for instance solubility and electrochemical behavior, and therefore widen the range of potential technical applications.
The Bingel reaction is a popular method in fullerene chemistry. The
malonate (functionalized with the
halide atom) is often obtained
in situ in a mixture of
base and
tetrabromomethane or
iodine.[2] The reaction is also known to take place with the
ester groups replaced by
alkyne groups in dialkynylmethanofullerenes.[2]
An alternative to the Bingel reaction is a fullerene
diazomethane reaction. N-(Diphenylmethylene)glycinate Esters [3] in a Bingel reaction take a different conjugate course and react to a fullerene
dihydropyrrole.
^Graham E. Ball; Glenn A. Burley; Leila Chaker; Bill C. Hawkins; James R. Williams; Paul A. Keller & Stephen G. Pyne (2005). "Structural Reassignment of the Mono- and Bis-Addition Products from the Addition Reactions of N-(Diphenylmethylene)glycinate Esters to [60]Fullerene under Bingel Conditions". J. Org. Chem.70 (21): 8572–8574.
doi:
10.1021/jo051282u.
PMID16209611.
^Kessinger, Roland; Crassous, Jeanne; Herrmann, Andreas; Rüttimann, Markus; Echegoyen, Luis; Diederich, François (1998). "Preparation of Enantiomerically Pure C76 with a General Electrochemical Method for the Removal of Di(alkoxycarbonyl)methano Bridges from Methanofullerenes: The Retro-Bingel Reaction". Angewandte Chemie International Edition. 37 (13–14): 1919.
doi:
10.1002/(SICI)1521-3773(19980803)37:13/14<1919::AID-ANIE1919>3.0.CO;2-X.
^Herranz, M. ÁNgeles; Cox, Charles T.; Echegoyen, Luis (2003). "Retrocyclopropanation Reactions of Fullerenes: Complete Product Analyses". The Journal of Organic Chemistry. 68 (12): 5009–12.
doi:
10.1021/jo034102u.
PMID12790625.
^Moonen, Nicolle N. P.; Thilgen, Carlo; Diederich, François; Echegoyen, Luis (2000). "The chemical retro-Bingel reaction: selective removal of bis(alkoxycarbonyl)methano addends from C60 and C70 with amalgamated magnesium". Chemical Communications (5): 335.
doi:
10.1039/a909704j.