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ortho effect on the nitrosation of the 2,3‐diphenyl‐5(2‐methoxyphenyl)pyrrole
Author(s) -
Ceraulo Leopoldo,
Agozzino Pasquale,
Ferrugia Mirella,
Sprio Vincenzo
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270226
Subject(s) - chemistry , nitrosation , pyrrole , sodium ethoxide , sodium nitrite , reactivity (psychology) , ethanol , medicinal chemistry , hydrogen bond , organic chemistry , molecule , medicine , alternative medicine , pathology
Abstract 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 N H and the ortho ‐methoxy group.