Unprecedented Double aza-Michael Addition within a Sapphyrin Core
authors Figueira, F; Marques, I; Farinha, ASF; Tome, AC; Cavaleiro, JAS; Silva, AMS; Sessler, J; Felix, V; Tome, JPC
nationality International
journal CHEMISTRY-A EUROPEAN JOURNAL
author keywords anions; cycloaddition; density functional calculations; Michael addition; porphyrinoids
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
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.
publisher WILEY-V C H VERLAG GMBH
issn 0947-6539
year published 2016
volume 22
issue 40
beginning page 14349
ending page 14355
digital object identifier (doi) 10.1002/chem.201602313
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000384698200011
  ciceco authors
  impact metrics
journal analysis (jcr 2017):
journal impact factor 5.160
5 year journal impact factor 4.950
category normalized journal impact factor percentile 78.655
dimensions (citation analysis):
altmetrics (social interaction):



 


Apoio

1suponsers_list_ciceco.jpg