78 Polynitropolycycloalkanes
OH
OH
OH
OH
Br
Br Br
Br
O
O
Br
Br
O
O O
O
Br
Br
Br
Br
O OO O
Br Br
HOOC
COOH
COOH
HOOC
ClOC COCl
ClOC
COCl
CO 2 CH 2 C(NO 2 ) 3
(O 2 N) 3 CH 2 CO 2 C
(O 2 N) 3 CH 2 CO 2 C
CO 2 CH 2 C(NO 2 ) 3
SOCl 2
(NO 2 ) 3 CCH 2 OH
+
(^818283)
85b85a 84a 84b
86a 86b 87a 87b
88a
88b
hv, benzene
- KOH (aq)
- H+
O
Figure 2.18
2.6 Prismanes
NO 2
O 2 N
O
O N N
OH
HO
Br
Br
NO 2
O 2 N
(^8990)
91
(^9392)
7 steps
NH 2 OH.HCl
NaOAc, MeOH
89 %
- Br 2 , DMF,
NaHCO 3 - TFAA, H 2 O 2 ,
CH 2 Cl 2
8 % (2 steps)
Bu 3 SnH, PhH,
reflux
50 %
Figure 2.19