第十八章 其它含氮化合物

1、 CH3 CH3 NO2 CH3NO2NO2 nitrobenzene 2-nitropropane RN+ O O- RN+ O O- 简写为： RN O O RNO2 RNO2RNO R NH OH RNH2 RNO NN+ O- RR RNO N N R R NH NHR R NH NHR R R NH OH RNO NN+ O- RR OH - RNO2 NN+ O- RR OH - As2O3 RNH2 RNO NN RR OH - NH NHR R RNO2 OH - NN RR OH2 Zn 取代羟胺 RNO2 R NH OH Zn NH4Cl OH2 H5C6NO2 OH2 A

2、s2O3 NN+ O- C6H5H5C6 H5C6NO2 OH2 N N C6H5 H5C6 Zn NO2 CH3 OH ZnOH - NH NH NO2 CH3 CH3 OH ZnOH - NH NH CH3 CH3 NH NHH5C6 C6H5 Na CH3 OH H5C6NH2 N N C6H5 H5C6 Na CH3 OH H5C6NH2 NN+ O- C6H5H5C6 Na CH3 OH H5C6NH2 OHO2N ClO2N NaOH NH2O2N ClO2N NH3 O O2N CH3 ClO2N N CH3 CH3 CH3 CH3 OH NHO2N C6H5 NO2 O O2N

3、NO2 C6H5 NH2C6H5 OO2N NO2 Et NO2 Me OK O N+ Me NO2 OEt NO2 -O KO ONO2 O2N Me O2N EtKO NH2 NO2F F FF FF NO2 FF F FF NO2 FNH2 F NH3 + 不共轭硝基氯原子不被氨基取代 Cl CH3 CH3 NO2 CH3 NO2 CH3 Cl NH3 O 2N CH3 CH3 NH2 CH3 NO 2 CH3 O2N NH3 不共轭硝基被氨基取代 NO2 NO2 CH3 CH3 NH3 NO2 NH2 CH3 CH3 NO2 CH3 O2N NH3 NH2 CH3 O2N Cl NO2

4、 O2N KCNS SCN NO2 O2N + NCS NO2 O2N NCS- N-CS Cl NO2 O2N CH3 O-Na+ O NO2 O2N CH3 O2N CH2 R OH3 + NaOH CH N+R OH O- O2N CH2 R NaOH CH R1 OHR NO2 R1CHO NO 2 CH 2 CH3 NaOH OH NO 2 CH3 CH3 CHO CH3 + O2N CH 2 R NaOH CH H5C6 R NO 2 H5C6CHO NO2CH2 CH3 NaOH CH3 NO2 CHO + 1-苯-2-硝基丙烯 NO2 CH2 R NaNO2 HCR Cl H

5、DMF R CH2 O NO + N O O - N O O - NO R N+N+ O- -O R R ONOH NON CH3 CH3 NaOH CH2N2 H5C6 H5C6 N2 O OCH3 N2 H5C6COOH NaOH CH2N2 + H5C6 O N CH3 NO NaOH CH2N2 N CH3 NO CH3 CH3 CH3 O CH3 O CH3 CH3 + H5C6 H5C6 N NH2 HgO H5C6 H5C6 N2 O OCH3 NH2 O OCH3 N2 HNO2 CH3COOH CH2N2 CH3COOMe HO3SOHHO3SO CH3 CH2N2 CH2N

6、2 ClH CH3Cl CH3 CH3 O OH CH2N2 CH3 CH3 O OCH3 CH2NN CH2 - N + N CH2 - N2 + R OH CH3N2 + RO- RO CH3 + N2 CH3 CH3 O CH2N2 CH3 CH3 O- CH2 N2 + CH3 CH3 O- CH2 N2 CH3 CH3 O NN + + CH3 CH3 O CH2N2 CH3 CH3 O- CH2 N2 + CH3 CH3O NN CH3 CH3 O- CH2 N2 + + CH2CO CH2N2 NN O + CH2CO CH2N2 CH2 CH2 N2+ -O NN O + R

7、Cl O CH2N2 R O Cl Cl O CH2N2 O Cl R Cl O CH2N2 R Cl O- CH2 N2+ R Cl O- CH2 N2+ R O N+N H R O N+N H R O N+ N: H+ R O N+ N: ClH R O Cl CH2N+N: CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH 2 N + N: R R RR + CH2N+N:CH2 R R RR CH2N+N: CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 R Cl O CH2N2 R O N+ N: Ag2O CR O R O N+N H R O N

8、 N: Cl- ClH CH2N2 ClH CH3Cl R O H Cl N2 CR O OH2 RCOOH CR O CH3OH R O OCH3 Cl O CH2N2 O N + N: Ag2O C O CH3OH C O C O O CH3 Cl O OH O SOCl2 CH2N+N:CH2 R R RR CH2N+N: CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH COOEt R R R R COOEt N N: EtOOC CH COOEt R R Zn / CuSO4 / HCl RR CH2I2 CH3 Zn / CuSO 4 / HCl CH3 CH2

9、I2 CH3Cl base CH2 - Cl CH2 Br Br HCBr3 t-BuOK / t-BuOH RN + NR + + N N N+N RN + NBr - CH3 CH3 NH2 CH3 CH3 N+ N HNO2 CH3 CH3 N N OH OH N+N Cl ClCl Cl NH2 COOH NaNO2 / H2SO4 Cl ClCl Cl N+ COOH N NH2N + N NaNO2 / HCl RN + N RNH2 CH3COOH NO O C5H11 RN + NBF 3 ArN + N OH2 ArNN OH OH - ArNN O - N + N C +

10、OH2 OH C + I- I N+NI KI N+N H H3PO2 N+N H NaBH4 N+N CN K CN CuCN CuXCuX2 X ArN2+ CuX2N2 Ar. + CuX2 CuXAr-X + Ar. CuX2 N+N NH2 NaNO2 HBF4 N + NF B - F F F F N + N N + N NO 2 NaNO 2 NaBF 4 BF 4 Cu N+N NH NH2 SnCl2 N+N OH NN OH N+N OH NN OH NN NaBH4 NH NH CH3 O O OH NN NN+ O- H2SO4 NH2NH2 NH NH H2SO4 N

11、H2NH2 CH3 CH3 NH NH CH3 CH3 H2SO4 NH2NH2 Cl Cl NH NH Cl Cl CH3 NO2CH3CH3 CH3CH3 CH3CH3 NH2NH2 NH NH CH3 CH3 NO2 CH3 NO2 CH3 CH3 OH ZnOH - NH NH CH3 CH3 CH3CH3 NH2NH2NH NH CH3 CH3 H2SO4 CH3CH3 CH3CH3 NH2NH2 1 H NO2 2 H3PO2 NO2 BrBr Br Br BrBr Br Br NH2NH2 Br Br NH NH Br Br NO2 Br NO2 NO2 FeBr3 BrBr N

12、O2 Br CH3 OH ZnOH - NH NH Br Br H2SO4 NH2NH2 Br Br BrBr Br Br 1 H NO2 2 CuBr BrBr BrBr R N- N+ N R N N+ N- N2- N+ N N- N+ N- N2- N+ N RBr NaN3 RN3 BrR O NaN3 N3 R O O NaN3 OH N3 N+ N: EtOOC NaN3 EtOOC N3 NH2 R LiAlH4 N3 R O NH2 CH3 Pt / H 2 N3 CH3 NCH3 O N3 CH3 O NCH3 O N C O CH3 O NH R OCH3 N3 R O CH3 OH