abstract
The azomethine ylide generated from the reaction of a corrole-3-carbaldehyde and N-methylglycine was trapped with dimethyl fumarate, dimethyl acetylenedicarboxylate and fullerene C(60) in 1,3-dipolar cycloadditions. A similar azomethine ylide generated from a corrole-2-carbaldehyde was trapped with 1,4-naphthoquinone, yielding the expected dehydrogenated 1,3-dipolar cycloadduct and a quinone-fused corrole derivative. A detailed synchrotron single-crystal X-ray diffraction analysis of the gallium(III)(pyridine) complex of 5,10,15-tris(pentafluorophenyl) corrole-3-carbaldehyde is also presented.
keywords
DIELS-ALDER REACTIONS; BARRELENE-FUSED CHLORINS; MESO-TETRAPHENYLPORPHYRIN; EFFICIENT SYNTHESIS; SYNTHETIC APPROACH; AZOMETHINE YLIDES; PORPHYRINS; DERIVATIVES; 5,10,15-TRIPHENYLCORROLE; TETRAARYLPORPHYRINS
subject category
Chemistry
authors
Vale, LSHP; Barata, JFB; Santos, CIM; Neves, MGPMS; Faustino, MAF; Tome, AC; Silva, AMS; Paz, FAA; Cavaleiro, JAS
our authors
Filipe Alexandre Almeida Paz
Principal Researcher
Joana Filipa Brites Barata
Post-doc Fellowshipacknowledgements
Thanks are due to the University of Aveiro, Fundacao para a Ciencia e a Tecnologia (FCT) and FEDER for funding the Organic Chemistry Research Unit and the project POCI/QUI/57589/2004. JFB Barata also thanks FCT for her PhD grant (SFRH/BD/18260/2004). We are also grateful to the European Synchrotron Radiation Facility in Grenoble (France) for granting the access time to the BM01a beam line.