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On the Reaction of Nitrilium Salts with Secondary Carboxamides
Author(s) -
Hitzler Martin G.,
Lutz Martin,
ShresthaDawadi Prativa Bade,
Jochims Johannes C.
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960215
Subject(s) - chemistry , salt (chemistry) , beckmann rearrangement , reaction mechanism , medicinal chemistry , polymer chemistry , organic chemistry , oxime , catalysis
Nitrilium salts 1 , the first products of the Beckmann rearrangement of oximes, react with secondary amides 2 , the final products of this rearrangement, to afford mixtures of up to four different N ‐acylamidinium salts 3–6 (mechanism Scheme 4 ). The ratio 3/4/5/6 depends on the configuration of 2 , the substituents of 1 and 2 , the reaction temperature and the concentrations of the reactants. With tertiary amides nitrilium salts give only one N ‐acylamidinium salt, the formation of which is also explained by the mechanism of Scheme 4 . An X‐ray structural analysis in reported for the product obtained from 2‐pyridone and N ‐isopropylbenzonitrilium hexachloroantimonate. First cyclic nitrilium salts ( 1d, k, w ) were prepared.