A Study on Deketalization of Rigid <TEX>${\beta}$</TEX>-Aminoketones
A Study on Deketalization of Rigid ${\beta}$-Aminoketones
Journal of the Korean Chemical Society. 1988. Dec, 32(6): 557-566
  • Published : December 20, 1988
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Kim, Jack C.
Lee, Yong Tae
Yoon, Ung Chan
Cho, In-Seop
Moon, Sung Hwan
Han, Sun Hong

The causes of failure in the deketalization of rigid ${\beta}$-aminoketals were separately investigated by examining the deketalization of 3 ketals, 2-ethylenedioxy-l-acenaphthenylamine (2), N-(2-ethylenedioxy-l-acenaphthenyl)acetamide(13) and trimethyl-2-ethylenedioxy-1-acenaphthenylammonium iodide(14), and by examining the deketalization of non-rigid ${\beta}$-aminoketal, 2-amino-l-ethylenedioxyacetophenone(19) and non-rigid aliphatic acetals, dimethylaminoformaldehyde dimethylacetal (20) and 2-aminoactaldehyde dimethyl acetal(21). While compounds 2 and 14 were not able to be hydrolyzed in the various acidic conditions 13 was easily deketalized. The result indicated the importance of electrostatic repulsion in the possible dicationic intermediates as a factor of failure in the deketalization. The observations of easy deketalization of compounds 19, 20 and 21 indicated that the structural characters of rigid $\beta-aminoketals$ are also important factors in the hydrolysis of ${\beta}$-aminoketals.