Organic Chemistry of Explosives

Dibenzotetraazapentalenes 325

NH 2

NH 2

N

H 2 N

NH 2

222

N

N 3

N 3

223

N

N

N

N 3

N

N

N

O 2 N

N

N

N

N

NO 2

NO 2

O 2 N

O 2 N

N

N

N

N

PbO 2

o-C 6 H 4 Cl 2

58 °C, 70 %

o-C 6 H 4 Cl 2

o-C 6 H 4 Cl 2

180 °C, 93 %

P(OEt) 3

221

(^226220224)

1. HNO 2


2. NaN 3
   93 %

xylene, reflux 180 °C, 95 %

82–88 %

90 % HNO 3 ,

H 2 SO 4

225

(z-TACOT)

N N

Figure 7.80

NH 2

NH 2

P(OEt) 3

Cl

NO 2

NH 2

NH

NO 2

N

N

N

NO 2

N

N

N

N 3

N

N

N N NO 2

NO 2

O 2 N

O 2 N

N

N

N N

EtOH

o-C 6 H 4 Cl 2

221

231

(y-TACOT)

xylene,

reflux 61–65 %

HNO 3 , H 2 SO 4

+

227

228 229

230

91

or 90 % HNO 3

58 %

NaNO 2 ,

AcOH

90 %

reflux

74 %

1. PtO 2 ,
   H 2 , 95 %


2. HNO 2 ,
   NaN 3 ,
   99 %

Figure 7.81

Treatment of the isomeric 1,3a,4,6a- (220) and 1,3a,6,6a- (91) dibenzotetraazapental-

enes with mixed acid or fuming nitric acid forms z-TACOT (225) and y-TACOT (231),

respectively.^137 ,^138 z-TACOT (225) and y-TACOT (231) are highly insensitive to impact

and electrostatic charge and exhibit extremely high thermal stability (ignition temperature

∼ 494 ◦C, DTA curve 354◦C).