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Highly Efficient Fluorine‐Promoted Intramolecular Condensation of Benzo[ c ]phenanthrene: A New Prospective on Direct Fullerene Synthesis
Author(s) -
Amsharov Konstantin Yu.,
Kabdulov Mikhail A.,
Jansen Martin
Publication year - 2009
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.200900976
Subject(s) - chemistry , phenanthrenes , intramolecular force , fluorine , phenanthrene , fullerene , condensation , selectivity , surface modification , condensation reaction , flash vacuum pyrolysis , organic chemistry , photochemistry , combinatorial chemistry , pyrolysis , catalysis , physics , thermodynamics
Various functional groups have been tested as alternative promoters of the intramolecular condensation of benzo[ c ]phenanthrene under flash vacuum pyrolysis conditions. Methyl and fluorine functionalization were found to be promising approaches. Unexpectedly high selectivity was observed in the cyclization of fluorinated benzo[ c ]phenanthrenes. The mechanism for the condensation reaction and the advantages of fluorine as a promoter for the rational synthesis of fullerenes are discussed.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)