The reaction of 5,10,15-tritolylcorrole with 3-dimethylaminoacrolein (3-DMA) and POCl3 gives a further example of the rebel reactivity of this contracted macrocycle. While no evidence was obtained for the formation of the expected -acrolein corrole, the inner core substituted N21,N22-3-formylpropylcorrole and the 10-acrolein isocorrole were the reaction products. By increasing the temperature or the amount of the Vilsmeier reagent, the 10-isocorrole became the unique reaction product. The formation of the isocorrole by electrophilic attack of the Vilsmeier reagent to the 10-position of the corrole is unprecedented in the porphyrinoids field and it could pave the way for a novel route to the preparation of stable isocorroles
Caroleo, F., Petrella, G., Di Zazzo, L., Nardis, S., Berna Berionni, B., Cicero, D.o., et al. (2020). A leopard cannot change its spots: Unexpected products from the vilsmeier reaction on 5,10,15-tritolylcorrole. MOLECULES, 25(16) [10.3390/molecules25163583].
A leopard cannot change its spots: Unexpected products from the vilsmeier reaction on 5,10,15-tritolylcorrole
Caroleo F.;Petrella G.;Nardis S.;Cicero D. O.;Paolesse R.
2020-01-01
Abstract
The reaction of 5,10,15-tritolylcorrole with 3-dimethylaminoacrolein (3-DMA) and POCl3 gives a further example of the rebel reactivity of this contracted macrocycle. While no evidence was obtained for the formation of the expected -acrolein corrole, the inner core substituted N21,N22-3-formylpropylcorrole and the 10-acrolein isocorrole were the reaction products. By increasing the temperature or the amount of the Vilsmeier reagent, the 10-isocorrole became the unique reaction product. The formation of the isocorrole by electrophilic attack of the Vilsmeier reagent to the 10-position of the corrole is unprecedented in the porphyrinoids field and it could pave the way for a novel route to the preparation of stable isocorrolesFile | Dimensione | Formato | |
---|---|---|---|
molecules-25-03583-v2.pdf
accesso aperto
Tipologia:
Versione Editoriale (PDF)
Licenza:
Creative commons
Dimensione
3.22 MB
Formato
Adobe PDF
|
3.22 MB | Adobe PDF | Visualizza/Apri |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.