Page 1031 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Scheme 11.1. Aromatic Nitration 1007
CN SECTION 11.1
CH 2
1 a CH 2 CN
Electrophilic Aromatic
Substitution
HNO 3
H SO 4
2
50–54%
NO 2
2 b
N(CH )
N(CH 3 ) 2 3 2
H SO 4
2
HNO 3
56–63%
NO 2
3 c CO 2 H CO 2 H
H SO 4
2
HNO 3 O N NO 2 54–58%
2
4 d
CH O CH O CH O CH O
3
3
HNO 3
3
O CH O NO 2 73–79%
CH 3
5 e
CH CHCH O CH CHCH O
HNO 3
Ac 2 O 36–46%
NO 2
6 f
CO 2 H CO 2 H
+ –
NH NO 3
4
(CF 3 CO) O
2
NO 2 94%
7 g CH CH 3
CH 3 HNO 3 3
2
CN (CF CO) O CN O N CN
2
3
(CH CO) O
2
3
zeolite β 87% 13%
NO 2
8 h La(NO ) ,
3 3
CO 2 CH 3 O N CO CH 3
2
2
NaNO 3
NHCO CH NHCO CH
HO 2 3 HCl HO 2 3
85%
9 i CH
30 mol% Sc(O SCF ) CH 3
CH 3 3 3 3 3
LiNO , (CH CO) O + NO 2
3
2
3
CH CN
3
CH 3 CH 3 CH 3
NO 2
68% 17%
(Continued)