The effect of steric hindrance in the synthesis of corrolates via the cobalt catalyzed cyclization of 2-(α-hydroxyalkyl)pyrroles
摘要:
2-(alpha-Hydroxyalkyl)pyrroles react in the presence of cobalt ions leading to the formation of corrolates or porphyrinates as a function of the 2-substituents. The nature of the cyclic tetrapyrrole obtained can be related to the steric hindrance of the substituent present in the starting pyrrole, The presence of cobalt ions is essential to drive the reaction towards the formation of the contracted corrole macroring. When 3-ethyl-4-methyl-2-(alpha-hydroxybenzyl)pyr acid is used as starting material an etio-like cobalt correlate, i.e. with alternate methyl and ethyl groups on the beta-pyrrolic positions, has been obtained as demonstrated by detailed analysis of the NMR spectrum of the complex, A possible reaction pathway explaining the formation of such a species is reported.