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Cover Picture: Imidazo[1,5‐ a ]pyridinium Salts from Phenylchlorocarbene and 2‐Pyridyl Schiff Bases: Synthesis, Reaction Mechanism and Effect of Rotamerism (Eur. J. Org. Chem. 24/2006)
Author(s) -
Bonneau Roland,
Guionneau Philippe
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200690048
Subject(s) - chemistry , pyridinium , carbene , ylide , schiff base , diazirine , substituent , medicinal chemistry , flash photolysis , thermal decomposition , alkyl , aryl , azide , photochemistry , polymer chemistry , organic chemistry , reaction rate constant , catalysis , physics , quantum mechanics , kinetics
The cover picture shows the mechanistic scheme of the synthesis of imidazo[1,5‐ a ]pyridinium salts from phenylchlorodiazirine and 2‐pyridyl Schiff bases. The carbene produced by thermolysis of the diazirine reacts with the pyridyl Schiff base to give two different ylide species, which are detected by laser flash photolysis. However, a single product is formed in a nearly quantitative yield and is easily separated from the reactants since it precipitates in nonpolar solvents. Colour code: blue = N, red = Cl, yellow = alkyl or aryl substituent, green = phenyl group. Details are discussed in the article by R. Bonneau and P. Guionneau on p. 5459 ff.