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Exploration of meso ‐Substituted Formylporphyrins and Their Grignard and Wittig Reactions
Author(s) -
Dahms Katja,
Senge Mathias O.,
Bakar M. Bakri
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700380
Subject(s) - chemistry , wittig reaction , grignard reaction , porphyrin , steric effects , reactivity (psychology) , residue (chemistry) , medicinal chemistry , reaction conditions , organic chemistry , catalysis , medicine , alternative medicine , pathology , reagent
Formylporphyrins were prepared by using either the 1,3‐dithian‐2‐yl residue as a precursor for the CHO group or by the Vilsmeier reaction. Two synthetic routes for the introduction of the 1,2‐dithian‐2‐yl group were explored. Furthermore, reactions of the 1,3,5‐trithian‐2‐yl group with porphyrins were examined as well as spirobisdithiane derivatives as precursors for the ultimate assembly of porphyrin spirobisdithanyl‐linked bioconjugates. The obtained formylporphyrins were reacted with organomagnesium or organophosphorus compounds. A series of hydroxyporphyrins resulting from the Grignard reaction of 5,15‐substituted porphyrins were synthesised in high yields. Several porphyrins with unsaturated residues introduced by the Wittig reaction were obtained in moderate yields. The less sterically hindered 5,15‐substituted porphyrins show increased reactivity and give higher yields; their reaction products are higher in stability relative to other porphyrin systems.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)