Identification of stable porphomethenes and porphodimethenes from the reaction of sterically hindered aldehydes with pyrrole

Authors
Senge, MO Runge, S Speck, M Ruhlandt-Senge, K
Citation
Mo. Senge et al., Identification of stable porphomethenes and porphodimethenes from the reaction of sterically hindered aldehydes with pyrrole, TETRAHEDRON, 56(45), 2000, pp. 8927-8932
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
45
Year of publication
2000
Pages
8927 - 8932
Database
ISI
SICI code
0040-4020(20001103)56:45<8927:IOSPAP>2.0.ZU;2-W
Abstract
Use of pivalaldehyde in mixed acid-catalyzed condensations of an aryl aldeh yde with pyrrole allows the isolation and structural characterization of st able porphomethenes (5,10,15,22-tetrahydroporphyrins) and porphodimethenes (both 5,10- and 5,15-diphydroporphyrins) as intermediates of porphyrin synt hesis. Crystal structures reveal the importance of the absolute configurati on at the sp(3)-hybridized centers for the oxidation and stability of these (bio)synthetic intermediates. (C) 2000 Elsevier Science Ltd. All rights re served.