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High‐field NMR study of the tautomers resulting from the condensation of 2‐methylindole and phenalenone in the presence of p ‐toluenesulphonic acid
Author(s) -
Tort F.,
Waegell B.,
Zahra J. P.,
Bernasconi C.,
Germanaud L.,
Bessibes C.,
Bounoure J.
Publication year - 1992
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260300802
Subject(s) - chemistry , tautomer , heteronuclear molecule , nucleophile , condensation , carbon 13 nmr , computational chemistry , medicinal chemistry , nuclear magnetic resonance spectroscopy , organic chemistry , catalysis , thermodynamics , physics
As phenalene is an alternant hydrocarbon it is oxidized very easily to phenalenone, which condenses with various nitrogen nucleophiles in the presence of p ‐toluenesulphonic acid. 2‐Methylindolylphenalene is obtained with 2‐ methylindole, together with other products. This product is a mixture of five tautomers in equilibrium, and these were analysed by homo‐ and heteronuclear two‐dimensional high‐field NMR (500 MHz) spectroscopy.