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Vilsmeier Formylation of 5,10,15‐Triphenylcorrole: Expected and Unusual Products
Author(s) -
Paolesse Roberto,
Nardis Sara,
Venanzi Mariano,
Mastroianni Marco,
Russo Michele,
Fronczek Frank R.,
Vicente Maria Graça H.
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200390136
Subject(s) - formylation , reagent , regioselectivity , chemistry , derivative (finance) , corrole , medicinal chemistry , organic chemistry , catalysis , financial economics , economics
Abstract 5,10,15‐Triphenylcorrole ( 1 ) reacts with the Vilsmeier reagent (POCl 3 /DMF) to give the corresponding 3‐formyl derivative 3 as the major product. The regioselectivity of the reaction was proven by X‐ray crystallography and only traces of the 2‐formyl isomer were observed. A more polar product is also observed and this compound becomes the major product when an excess of DMF is used for the preparation of the Vilsmeier reagent, while the formation of the 3‐formyl isomer is almost completely suppressed. X‐ray crystallography allowed us to identify this compound as the fully substituted N‐ethane bridged derivative 4 , formed from the attack of the Vilsmeier reagent at the inner core of the macrocycle. This compound is unique among porphyrinoid macrocycles, and further confirms the peculiarity of corrole chemistry.