1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26
18
no Lewis acid required because aniline is very reactive on its own.
2.8.
Benzene Diazonium Salts
2.8.1.Primary Aromatic Amines
General reaction scheme:
Mechanism
NH2
Br
NHCOCH3
vs
Br2/ xs
Br2
Ac2O
NO2
R
NX 2
reduction
Sn / HCl or H2 / Pt
HCl / NaNO2
< 5oC
unstable above 5oC
also H2SO4/ NaNO2 involves less nucleophilic counter ion HSO- 4