Organic Chemistry of Explosives

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

  
  

1. KOH (aq)


2. 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 %

1. Br 2 , DMF,
   NaHCO 3


2. TFAA, H 2 O 2 ,
   CH 2 Cl 2
   8 % (2 steps)

Bu 3 SnH, PhH,

reflux

50 %

Figure 2.19