178 Synthetic Routes to AromaticC-Nitro Compounds
COOHCl
150COOHCl
151O 2 N NO 2NH 2Cl
152O 2 N NO 2N ClNO 2 NO 22 N NO 2 O 2 NO NO 22 N O 2 NOClH
NNO 2 NO 22 N NO 2 O 2 NO NO 2O 2 N O 2 NH
N
HN NN NHNNNHNNH 2 Noleum, HNO 3 ,
92–95 °C
81 %oleum, NaN 3
reflux
84 %H 2 SO 4 , HNO 3 ,
85–90°C, 78 %MeOH
64 %17
(BTDAONAB)153NN NFigure 4.67ClOMeMeONO 2
NO 2O 2 N
O 2 NNO 2
OMeMeOOMe
NO 2
155MeONO 2
O 2 N NO 2O 2 NNO 2
NH 2NH 2H 2 NNO 2
156H 2 N154- H 2 SO 4 , HNO 3 NH 3 , MeOH
- Cu powder,
xylene, reflux
Figure 4.68extremely insensitive to electrostatic discharge and has been used for seismic experiments on
the moon.^299
O 2 NO 2 NNO 2NO 2NO 2O 2 NH 2 N NH 2157
(DIPAM)Figure 4.69High molecular weight often results in an increase in thermal stability, probably from the
increase in melting point – decomposition is much more rapid in a melt than in the solid phase.
2,2′,2′′,4,4′,4′′,6,6′,6′′-Nonanitro-m-terphenyl (NONA) (158) is synthesized from the Ullman