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Photooxidation and Intramolecular Reaction of the Anthryl Moiety in [60]Fullerene Derivatives
Author(s) -
Irngartinger Hermann,
Weber Anton,
Escher Thomas
Publication year - 2000
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/(sici)1099-0690(200004)2000:8<1647::aid-ejoc1647>3.0.co;2-6
Subject(s) - chemistry , moiety , intramolecular force , anthracene , cycloaddition , fullerene , nitrile , photochemistry , adduct , singlet oxygen , fullerene chemistry , medicinal chemistry , organic chemistry , oxygen , catalysis
Anthracene groups have been linked to [60]fullerene by the [3+2] cycloaddition of the corresponding nitrile oxides or by esterification with a [60]fullerenol. The anthryl groups of the fullerene derivatives 3 , 7 , and 10 react readily with singlet oxygen to form the 9,10‐epidioxides 4 , 8 , and 12 under photooxidation. The anthryl moiety of the fullerenol ester 10 also reacts with the fullerene skeleton to form the stable intramolecular Diels‐Alder adduct 11 .