The regioselectivity in the nitrosation of seven N-methyl-N'-substituted phenylureas ($CH_3NHCONHC_6H_4-G$; G = H, p-CH$_3$, m-CH$_3$, m-CH$_3$O, p-F, m-F, m-Br) was examined using NaNO$_2$ and 4 different acids (diluted HCl, HCOOH, CH$_3$COOH, CF$_3$COOH). In all cases, the two regioisomeric products, N-nitroso-N-methyl-N'-substituted phenylureas (A) and N'-nitroso-N-methyl-N'-substituted phenylureas (B) were observed to be formed as major products and product ratios were determined by the integration of their methyl peaks in $^1$H-NMR. Electron donating substitutent(G) on phenyl of the ureas generally led to increase the ratio of B to A. The data have revealed that the relative sensitivity of the nitrosonium species (HONO, HCOONO, CH$_3$COONO, CF$_3$COONO) toward the change of electron density on nitrogen with phenyl substitutents are 1.00 : 0.93 : 0.78 : > �� 0.7.
Citing 'The Reactivity and Regiochemical Effect of Nitrosonium Species in the Nitrosation of N-Methyl-N'-Substituted Phenylureas
'
@article{ JCGMDC_1991_v35n3_240}
,title={The Reactivity and Regiochemical Effect of Nitrosonium Species in the Nitrosation of N-Methyl-N'-Substituted Phenylureas}
,volume={3}
, number= {3}
, journal={Journal of the Korean Chemical Society}
, publisher={Korean Chemical Society}
, author={Jack C., Kim
and
In-Seop, Cho
and
Soon-Kyu, Choi}
, year={1991}
, month={Jun}
TY - JOUR
T2 - Journal of the Korean Chemical Society
AU - Jack C., Kim
AU - In-Seop, Cho
AU - Soon-Kyu, Choi
SN - 1017-2548
TI - The Reactivity and Regiochemical Effect of Nitrosonium Species in the Nitrosation of N-Methyl-N'-Substituted Phenylureas
VL - 35
PB - Korean Chemical Society
PY - 1991
ER -
Jack C., K.
,
In-Seop, C.
,
&
Soon-Kyu, C.
( 1991).
The Reactivity and Regiochemical Effect of Nitrosonium Species in the Nitrosation of N-Methyl-N'-Substituted Phenylureas.
Journal of the Korean Chemical Society,
35
(3)
Korean Chemical Society.
Jack C., K
,
In-Seop, C
,
&
Soon-Kyu, C
1991,
The Reactivity and Regiochemical Effect of Nitrosonium Species in the Nitrosation of N-Methyl-N'-Substituted Phenylureas,
Journal of the Korean Chemical Society,
vol. 3,
no. 3,
[1]
K Jack C.
,
C In-Seop
,
and
C Soon-Kyu
,
“The Reactivity and Regiochemical Effect of Nitrosonium Species in the Nitrosation of N-Methyl-N'-Substituted Phenylureas”,
Journal of the Korean Chemical Society,
vol. 3,
no. 3,
Jun
1991.
Jack C., Kim
and
,
In-Seop, Cho
and
,
Soon-Kyu, Choi
and
,
“The Reactivity and Regiochemical Effect of Nitrosonium Species in the Nitrosation of N-Methyl-N'-Substituted Phenylureas”
Journal of the Korean Chemical Society,
3.
3
1991:
Jack C., K
,
In-Seop, C
,
Soon-Kyu, C
The Reactivity and Regiochemical Effect of Nitrosonium Species in the Nitrosation of N-Methyl-N'-Substituted Phenylureas.
Journal of the Korean Chemical Society
[Internet].
1991.
Jun ;
3
(3)
Jack C., Kim
,
In-Seop, Cho
,
and
Soon-Kyu, Choi
,
“The Reactivity and Regiochemical Effect of Nitrosonium Species in the Nitrosation of N-Methyl-N'-Substituted Phenylureas.”
Journal of the Korean Chemical Society
3
no.3
()
Jun,
1991):
