The Effect of Substituents on the Dissociation Constants of Carboxylic Acids

1944 ◽  
Vol 12 (7) ◽  
pp. 277-288 ◽  
Author(s):  
James N. Sarmousakis
1974 ◽  
Vol 52 (4) ◽  
pp. 610-615 ◽  
Author(s):  
G. R. Birchall ◽  
A. H. Rees

We have investigated the ring expansion of some substituted 1,4-naphthoquinones by hydrazoic acid to yield new 1-benzazepine derivatives of the "azatropolone" type. Ring contraction of those products, which are 2,5-dihydro-3-hydroxy-2,5-dioxo-1-benzazepines, gives 4-quinolone-2-carboxylic acids. Some of the reactions of the new benzazepine system were investigated. Attempts to prepare substituted derivatives suitable for making 1-benzazatrop-5-one were not successful.The effect of substituents on the ring expansion reaction is discussed and an anomalous ring expansion to a 2,5-dihydro-4-hydroxy-2,5-dioxo-1-benzazepine is described and explained mechanistically.


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