abstract
The reactivity of porphyrinyl and corrolyl nitrones towards dipolarophiles bearing electron-withdrawing groups was studied and it was found that the two nitrones behave differently in 1,3-dipolar cycloaddition reactions. While porphyrinyl nitrone reacts with dimethyl fumarate, dimethyl acetylenedicarboxylate and ethyl propiolate to afford the expected isoxazolidine and isoxazoline cycloadducts, the corrolyl nitrone reacts with dimethyl fumarate to provide an isoxazolidine-substituted corrole but with dimethyl acetylenedicarboxylate it gives amide derivatives. (C) 2015 Elsevier Ltd. All rights reserved.
keywords
1,3-DIPOLAR CYCLOADDITION REACTIONS; ISOXAZOLINE-FUSED CHLORINS; ALKYL NITRILE OXIDES; MESO-TETRAARYLPORPHYRINS; PERIPHERAL FUNCTIONALIZATION; AZOMETHINE YLIDES; PORPHYRINS; BACTERIOCHLORINS; CORROLES
subject category
Chemistry
authors
da Silva, AFF; Barata, JFB; Silva, AMG; Neves, MGPMS; Tome, AC; Silva, AMS; Cavaleiro, JAS
our authors
Joana Filipa Brites Barata
Post-doc FellowshipGroups
acknowledgements
Thanks are due to Fundacao para a Ciencia e a Tecnologia (FCT, Portugal), European Union, QREN, FEDER and COMPETE for funding the projects PEst-C/QUI/UI0062/2011, PEst-C/EQB/LA0006/2011, NORTE-07-0162-FEDER-000048 and NORTE-07-0124-FEDER-000066/67 and the Portuguese National NMR Network, also supported by funds from FCT. J.F.B. Barata thanks FCT for the post-doctoral grant SFRH/BPD/63237/2009. A.F.F. Silva thanks QOPNA for a research grant.