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Functionalization of [60]Fullerene and of [60]Fullerene Monoadducts by Photochemical Cycloaddition of 4‐Methyl‐1,2,4‐triazoline‐3,5‐dione
Author(s) -
Ulmer Lars,
Siedschlag Christina,
Mattay Jochen
Publication year - 2003
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.200300297
Subject(s) - chemistry , cycloaddition , regioselectivity , fullerene , adduct , surface modification , photochemistry , double bond , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The photoreactions of 4‐methyl‐1,2,4‐triazoline‐3,5‐dione (NMTAD) with C 60 and with several fullerene derivatives have been studied. In general, NMTAD cycloadds to C 60 and to its monoadducts with closed structures in a highly regioselective [2+2] fashion at a cis ‐1 [6,6] double bond. Cycloadditions to azafulleroids occur by a slightly different pathway and result in partially cluster‐opened bis(adducts). 1,6‐Methano[60]fulleroid, however, also undergoes a [2+2+2] cycloaddition in the absence of light. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)