Title
Vilsmeier formylation of 5,10,15-Triphenylcorrole: Expected and unusual products
Document Type
Article
Publication Date
3-3-2003
Abstract
5,10,15-Triphenylcorrole (1) reacts with the Vilsmeier reagent (POCl3/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.
Publication Source (Journal or Book title)
Chemistry - A European Journal
First Page
1192
Last Page
1197
Recommended Citation
Paolesse, R., Nardis, S., Venanzi, M., Mastroianni, M., Russo, M., Fronczek, F., & Vicente, M. (2003). Vilsmeier formylation of 5,10,15-Triphenylcorrole: Expected and unusual products. Chemistry - A European Journal, 9 (5), 1192-1197. https://doi.org/10.1002/chem.200390136