Please use this identifier to cite or link to this item:
http://hdl.handle.net/10773/20925
Title: | Unprecedented Double aza-Michael Addition within a Sapphyrin Core |
Author: | Figueira, Flavio Marques, Igor Farinha, Andreia S. F. Tome, Augusto C. Cavaleiro, Jose A. S. Silva, Artur M. S. Sessler, Jonathan Felix, Vitor Tome, Joao P. C. |
Keywords: | 1,3-DIPOLAR CYCLOADDITION REACTIONS DIELS-ALDER REACTIONS BARRELENE-FUSED CHLORINS EXPANDED PORPHYRINS DIMETHYL ACETYLENEDICARBOXYLATE MESO-TETRAARYLPORPHYRINS PHOTOPHYSICAL PROPERTIES AZOMETHINE YLIDES ORGANIC-SYNTHESIS O-XYLYLENE |
Issue Date: | 2016 |
Publisher: | WILEY-V C H VERLAG GMBH |
Abstract: | A novel sapphyrin derivative was obtained from the reaction between a free-base sapphyrin and dimethyl acetylenedicarboxylate (DMAD). The formation of the new compound involved a double aza-Michael addition of two pyrrolic NH groups to a DMAD molecule, with the formation of a disubstituted ethano bridge. The NMR spectral data reveal a product with an unsymmetrical structure; DFT calculations provided support for a structure in which the ethano bridge links two adjacent pyrrole units. The present study provides a seemingly unprecedented example of an N,N'-dinucleophile reacting with DMAD to form a heterocyclic compound in which the two N-atoms are linked to the two sp(3) carbon atoms derived from a substituted acetylene. |
Peer review: | yes |
URI: | http://hdl.handle.net/10773/20925 |
DOI: | 10.1002/chem.201602313 |
ISSN: | 0947-6539 |
Publisher Version: | 10.1002/chem.201602313 |
Appears in Collections: | CICECO - Artigos |
Files in This Item:
File | Description | Size | Format | |
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Unprecedented Double aza-Michael Addition within a Sapphyrin Core_10.1002chem.201602313.pdf | 1.32 MB | Adobe PDF |
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