6533b834fe1ef96bd129d503
RESEARCH PRODUCT
orthoeffect on the nitrosation of the 2,3-diphenyl-5(2-methoxyphenyl)pyrrole
Vincenzo SprioMirella FerrugiaPasquale AgozzinoLeopoldo Ceraulosubject
chemistry.chemical_compoundEthanolSodium ethoxidechemistryHydrogen bondOrganic ChemistryNitrosationOrganic chemistryReactivity (chemistry)NitriteMedicinal chemistryPyrroledescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1990-02-01 | Journal of Heterocyclic Chemistry |