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.
Citing 'A Study on Deketalization of Rigid ${\beta}$-Aminoketones
'
@article{ JCGMDC_1988_v32n6_557}
,title={A Study on Deketalization of Rigid ${\beta}$-Aminoketones}
,volume={6}
, number= {6}
, journal={Journal of the Korean Chemical Society}
, publisher={Korean Chemical Society}
, author={Jack C., Kim
and
Yong Tae, Lee
and
Ung Chan, Yoon
and
In-Seop, Cho
and
Sung Hwan, Moon
and
Sun Hong, Han}
, year={1988}
, month={Dec}
TY - JOUR
T2 - Journal of the Korean Chemical Society
AU - Jack C., Kim
AU - Yong Tae, Lee
AU - Ung Chan, Yoon
AU - In-Seop, Cho
AU - Sung Hwan, Moon
AU - Sun Hong, Han
SN - 1017-2548
TI - A Study on Deketalization of Rigid ${\beta}$-Aminoketones
VL - 32
PB - Korean Chemical Society
PY - 1988
ER -
Jack C., K.
,
Yong Tae, L.
,
Ung Chan, Y.
,
In-Seop, C.
,
Sung Hwan, M.
,
&
Sun Hong, H.
( 1988).
A Study on Deketalization of Rigid ${\beta}$-Aminoketones.
Journal of the Korean Chemical Society,
32
(6)
Korean Chemical Society.
Jack C., K
et al.
1988,
A Study on Deketalization of Rigid ${\beta}$-Aminoketones,
Journal of the Korean Chemical Society,
vol. 6,
no. 6,
[1]
K Jack C.
,
L Yong Tae
,
Y Ung Chan
,
C In-Seop
,
M Sung Hwan
,
and
H Sun Hong
,
“A Study on Deketalization of Rigid ${\beta}$-Aminoketones”,
Journal of the Korean Chemical Society,
vol. 6,
no. 6,
Dec
1988.
Jack C., Kim
Yong Tae, Lee
Ung Chan, Yoon
et al.
“A Study on Deketalization of Rigid ${\beta}$-Aminoketones”
Journal of the Korean Chemical Society,
6.
6
1988:
Jack C., K
,
Yong Tae, L
,
Ung Chan, Y
,
In-Seop, C
,
Sung Hwan, M
,
Sun Hong, H
A Study on Deketalization of Rigid ${\beta}$-Aminoketones.
Journal of the Korean Chemical Society
[Internet].
1988.
Dec ;
6
(6)
Jack C., Kim
,
Yong Tae, Lee
,
Ung Chan, Yoon
,
In-Seop, Cho
,
Sung Hwan, Moon
,
and
Sun Hong, Han
,
“A Study on Deketalization of Rigid ${\beta}$-Aminoketones.”
Journal of the Korean Chemical Society
6
no.6
()
Dec,
1988):
