6533b86efe1ef96bd12cb2e2

RESEARCH PRODUCT

ChemInform Abstract: ortho Effect on the Nitrosation of the 2,3-Diphenyl-5-(2-methoxyphenyl)pyrrole.

Pasquale AgozzinoLeopoldo CerauloMirella FerrugiaVincenzo Sprio

subject

chemistry.chemical_compoundEthanolSodium ethoxidechemistryHydrogen bondNitrosationReactivity (chemistry)General MedicineNitriteMedicinal chemistryPyrrole

description

A comparison of the behaviour on the nitrosation of the isomers 5-(2-methoxyphenyl)- (1a) 5-(3-methoxyphenyl)- (1b) and 5-(4-methoxyphenyl)2,3-diphenylpyrroles (1c) carried out in the usual way with iso-amyl nitrite in a solution of sodium ethoxide in ethanol evidences that 1a is dramatically less reactive with respect to 1b and 1c. The different reactivity was ascribed to the occurrence of a strong hydrogen bond involving pyrrole NH and the ortho-methoxy group.

https://doi.org/10.1002/chin.199032136