Organic Chemistry of Explosives

336 Miscellaneous Explosive Compounds

NO 2

C

NO 2

FNCH 2 CH 2 CO 2 CH 2 CH(N 3 )CH 2 N 3 N 3 CH 2

CH 2 CF(NO 2 ) 2

CH 2 CF(NO 2 ) 2

18 19

Figure 8.7

HO N 3

N 3

20

HO N 3

N 3

21

Figure 8.8

The azidoalcohols (20) and (21) have been reacted with acid chlorides and alkyl chloride

to give esters containing both azido and fluorodinitromethyl functionality.^16 ,^17

C

NO 2

NO 2

22

TsOCH 2 CH 2 OCH 2 CH CH 2 C

NO 2

NO 2

23

N 3 CH 2 CH 2 OCH 2 CH(N 3 )CH 2 N 3

Ts = p-CH 3 C 6 H 4 SO 2

1. Br 2


2. NaN 3

Figure 8.9

The triazide (23) has been synthesized from the bromination of the tosylate (22) followed

by displacement of both bromide and tosylate functionality with sodium azide.^16

CH 3

C

CH 3

24

O 2 N CH 2 OH

CH 3

C

CH 3

25

O 2 N CH 2 OTs

CH 3

C

CH 3

26

O 2 N CH 2 N 3

TsCl, Pyr

88 %

NaN 3 , DMF (aq)

37 %

Figure 8.10

2-Methyl-2-nitro-1-azidopropane (26), synthesized from the tosylate (25), has been sug-

gested for use as an energetic plasticizer.^18

O

CH 2 N 3

CH 2 N 3 HOCH 2 C

CH 2 N 3

CH 2 N 3

29

O 2 NOCH 2 C

CH 2 N 3

CH 2 N 3

31

(PDADN)

N 3 CH 2 C

CH 2 N 3

CH 2 N 3

30

O

CH 2 Cl

CH 2 Cl

28

(BAMO)

70 % HNO 3 ,

CH 2 Cl 2

78 %

HNO 3 , Ac 2 O,

CH 2 Cl 2 , 84 %

27

95 °C

NaN 3 , DMF

1. 48 % HBr, CH 2 Cl 2


2. NaN 3 , DMSO

CH 2 ONO 2

CH 2 OH CH 2 ONO 2

Figure 8.11