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Side‐Chain Modifications of C 60 via Activation of the Easily Accessible Fulleromalonic Acid C 61 (COOH) 2
Author(s) -
Lamparth Iris,
Schick Georg,
Hirsch Andreas
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970136
Subject(s) - malonic acid , chemistry , diethyl malonate , decarboxylation , malonate , fullerene chemistry , acetic acid , saponification , fullerene , adduct , side chain , coupling reaction , organic chemistry , polymer chemistry , medicinal chemistry , catalysis , polymer
Side‐chain modifications of fullerenes can be achieved starting from the malonic acid 2 , which is easily accessible by saponification of the corresponding diethyl malonate adduct 1 and is therefore an ideal building block for side chain chemistry on fullerenes. Coupling reactions are carried out via the synthesis of the fullerene active ester 4 , which is formed by the reaction of the malonic acid 2 with N ‐hydroxysuccinimide. During this reaction the malonic acid undergoes decarboxylation, yielding an acetic acid derivative instead of a malonic system. The active ester 4 is isolable and represents an ideal building block for fullerene chemistry. Sidechain modifications can also be carried out as one‐step reactions by preparing 4 in situ. We have performed coupling reactions with various compounds containing primary or secondary amino groups.