10

( ).

,
.
.

 .
.

. , .
.
:
-, -, -,
.
:
, , CH, .
. -
,
. .


ArNH2 + NaNO2 + 2HCl
HNO2 + H3O

ArN

NCl + NaCl + 2H2O

H2O + H2NO2+

H2NO2 + NO2

O=N-O-N=O + H2O

H2NO2 + Cl

O=N-Cl + H2O

H2NO2 + Br

O=N-Br + H2O

NO >> H2NO2 > NOBr > NOCl > N2O3 >> HNO2

ArNH3 + H2O

ArNH2 + H3O

ArNH2 + O=N-X

X=Cl;Br;ONO

N N O+X
H H

H2O

H
ArN

Ar

N OH + H2O

H3O+

ArNH-N=O + H3O

ArN=N-OH + H3O

Ar
N N

ArN

+ H2O
O H
H

N + H2O

HNO2

BuOH
NH2

BuONO 85%

H2SO4
N

BuONO

O-

OH
O

-
NaNO2
NH2
O2 N

NO2

H2SO4

OSO3H
O N

OSO3H
O N
O2N

N2+
NO2


O
N

N
N

Ar

N N

N N
Ar

O
H3O

H2O

N N
Ar

H
O

N O + H2 O

ArNH

N N
Ar

H2O;H
-

+ H3O

+ H3O

+ 2OH

OH

Ar

+ H2O

N N + H2 O

t C

N N
Ar

Ar

N N

OH
H

Ar

N N
Ar

OH

O
-

H
Ar

N N OH

OH

N N O
H

N-

OH
Ar

N N OH
H

OH


O Na

N N
Ar
OAg
N N

RI

Ar

RI

20 C
CH3OH

Ar

70- 80 %

N N
Ar
OC2H5

-20 C
CH2Cl2

N N
60 -70 %

Ar

-20 C

N N
Ar

OR

-10 C

+ (C2H5)3OBF4

+ NaI

N N

O Na
N N

Ar

(C2H5)3OBF4

CH2Cl2

N N
Ar

C2H5
O

X + N2

( 1)

N2 + X

+ N2 + X

( 2)

N=N-X

( 3)

N 2 + Y-

( 4)

Y
Y


ArN2 X
ArN2

t C

+ H2O

CH3

ArOH + N2 + HX

H2O
Ar + N2

N N

H2O

H2O
H2SO4; 100 C

ArOH + H3O

CH3
92 % Br

Br

N N
O2N

OH

H2O

OH

H2SO4; 100 C
O2N

81- 85 %



ArN2 BF4

NH2
CH3

t C

HNO2

ArF + BF3 + N2

N2BF4

HBF4

200 o C

-N2, -BF3

CH3

CH3

69 %

F
BF4N2

N2BF4

180 o C

82 %

ArN2 Cl + HPF6

NH2
HOOC

Cl N2

H2O

COOH

NaNO2

ArN2 PF6

+ HCl

N2 PF6
COOH

HPF6

F
o

COOH

170 C

HCl

N2 SbF6
NO2

61 %

180o C
40 %

F
NO2

200o C
10 -15 %

N2 BF4
NO2


C6H5N2 Cl

Kl
C6H5I + N2 + KCl
H2O; 25 C
74 -76 %
N2 Cl

NH2

Kl
H2O
30- 40

NaNO2
H2SO4;H2O
5 C
NO2

NO2

C6H5N2 Cl

KSCN
H2O; 25 C

NO2
81 %

C6H5-S C N 54 %

 SRN

Nu

N2
Ar
+
ArN2 + e

ArN2

ArNu

ArNu

+
ArN2


NaNO2

Cu2Br2
HBr; 60 C

HBr; 0 -5 C
Cl

+ N2

NH2

Cl

Cl

N2

Br
80 -95 %

Cu2Cl2

NaNO2
HCl; 0 -5 0 C
CH3

HCl; 70 C
CH3

NH2

+ N2

CH3

N2

Cl

74 -79%

NH2

1) NaNO2; HCl; H2O

2) Cu Cl; 80 o C

Cl

NH2

Cl

70 %

1
ArN2 X +Cu X

CH3
NH2

NO2
NH2

O2N

ArX + CuI X

[Ar Cu ll X2] + N2

CH3

NaNO2
H2SO4, H2O; 5 0C

NaNO2

H2O; 5 0 C

CN
64 -70 %

NO2

K[Cu(CN)2]
H2O; 90-100 C
0

HCl, H2O; 5 C
0

N2 BF4

K[Cu(CN)2]

N2 HSO4

NO2

CH3

N2 Cl

NaNO2;Cu
H2O

CN
65 %

O2N

NO2 67-82 %

Ar

N N + NaN3
Cl

H2N

Ar

N N

+ NaCl

t C

Ar-N=N=N + N2

N N

Cl N2
NaNO2

N3
NaN3

HCl; H2O
88 %

S
NaNO2
NH2

HCl; 0-5 C

KS
N2 Cl

OC2H5

H2O; 40 C

S
KOH

OC2H5

H2O; 40 C

HCl
SH
63-75%

SK

O2N

NH2

NH2

NaNO2
0

H2SO4; 0 -5 C

O2N

NaNO2
H2SO4; 0 -5 0 C

C2H5OH
pH > 7
C6H6
100

C6H5N2

N2

C2H5OH
0

80 C

C2H5OH

N2

80 C

C2H5OH
pH < 1
C6H5OC2H5
90

O2N
70 %

OC2H5
58 %

 :
ArN2 + CH3OH

ArN2 + CH3OH
ArN2

Ar + N2

CH3OH

CH2OH + H
:
ArH + CH2OH

Ar + CH3OH

ArN2 + CH2OH

CH2OH + ArN2
O
CH2OH

HC

+H

ArN2 Cl + H3PO2 + H2O

0- 5 o C

H2O

ArH + H3PO3 + HCl + N2

;
ArN2 +H3PO2

Ar + N2 + H2PO2

+ H+

;
Ar + H3PO2

ArH + H2PO2

ArN2 + H2PO2

Ar +N2 + H2PO2

H2PO2 + 2 H2O

H3PO3 + H3O ..

N2

NH2
O2 N

NO2

O=N-OSO3H
10 -20oC

O2N

Br2

Br

HBr; H2O
NH2

Cl N2

O2N
H3PO2
H2O;0 -10oC

NO2

NO2

COOH

NO2

COOH
Br

NaNO2Br
HCl; o
NH2
0-5 C

Br

N2 Cl

NO2

60-65 % NO2

COOH
Br H PO Br
3
2
N2
Br

70-80 %

NaBH4

75 %

COOH
Br

Br

2
1
Ar N2 Cl + Ar H

Br

N2 Cl +

NaOH
HOH

1 2
Ar -Ar + N2 + NaCl

NaOH
-: 5 C

Br
35-40 %

N2 +C6H5NO2

NO2

NaOH
H2O; 0-5 o C
o-: -:n60 : 10 : 30

ArN2 + 2 OH
ArN2 + ArN=N-O
Ar-N=N-O-N=N-Ar

Ar-N=N-O + H2O
Ar-N=N-O-N=N-Ar
Ar-N=N-O + Ar + N2
Ar

Ar

+
H

Ar

+ Ar-N=N-O

Ar-C6H5 + Ar-N=N-OH

H
Ar
H

+ ArN2

ArC6H5 + Ar + N2 + H

ArN2 Cl + CH2=CHX

Cu2Cl2

X=CN;COOR

ArCH2CHX + N2
Cl


-
ArN2 +

Ar-N=N

X=OH; NH2

X=O- > NR2 > NHR > NH2~OR >> CH3 (Alk)
ArH + Ar

N N

k1

Ar

k-1

k2[B]
N=N-Ar

1
ArN=NAr + BH

N
N

+
-

O3S

N
HO3S

ArN2 +

ArN

N-O

ArN

N
H

ArN

OH

ArN2 + H2N

Ar-N=N-NH2

H
ArN=N

NH2
H
Ar-N=N-NH

NH

ArN=N

NH2 + BH

NH2
NH2

NH2

HNO2

H
N
N

 CH-

N
+

OEt

EtO
O

EtO

N
OEt
O

NH

EtO

OEt
O

ArN2 X

Na2SO3

ArN=NSO3Na

H2O; 0 0C

H
ArN

N SO3Na

SO3Na

HCl
0

H2O t C

ArN2 Cl +2SnCl2 + 4HCl

0 -10 0 C

NaHSO3
H2O

ArNH-NH2 HCl

ArNH-NH2 HCl + 2 SnCl4

Cl

NO2
N2

Cl

NO2

NO2
H2O

N2

OH
Cl

NO2
NH2

NaNO2
HCl; 0 C

N2 Cl

NCS

N2 Cl + SCN

N2 Cl

H2O

HCl; 5 C

N2 Cl