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Sequential Fullerenylation of Bis‐malonates – Efficient Access to Oligoclusters with Different Fullerene Building Blocks
Author(s) -
Wasserthal Lennard K.,
Kratzer Andreas,
Hirsch Andreas
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300122
Subject(s) - chemistry , cyclopropanation , malonate , fullerene , adduct , nucleophile , octahedron , halogen , base (topology) , medicinal chemistry , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , crystal structure , mathematical analysis , alkyl , mathematics
A method for the sequential fullerenylation of bis‐malonates with parent C 60 and C 2 v ‐symmetric pentakis‐adducts is reported. This approach relies on the finding that (a) chloromalonates can be used for the nucleophilic cyclopropanation of [6,6] double bonds of C 60 , and (b) chloromalonates, in contrast to bromomalonates, do not undergo base‐catalyzed halogen exchange reactions. For the proof of concept, we synthesized a heptafullerene by using a divergent approach based on a fullerene hexakis‐adduct with six bis‐malonate addends in octahedral positions, each of which is suitable for an additional cyclopropanation of a fullerene building block.