Tetrahedron

A convenient s rn 1 synthesis of aromatic nitriles from diazonium salts via diazosulfides

G Petrillo, M Novi, G Garbarino, C Dell'erba

Index: Petrillo, Giovanni; Novi, Marino; Garbarino, Giacomo; Dell'erba, Carlo Tetrahedron, 1987 , vol. 43, # 20 p. 4625 - 4634

Full Text: HTML

Citation Number: 31

Abstract

Properly substituted diazosulfides XC6H4-N= N-SPh (1)(either isolated or generated in situ from arenediazonium tetrafluoroborates and sodium benzenethiolate) react with tetrabutylammonium cyanide, in Me2SO under photon or electron stimulation, leading to nitriles XC6H4CN (2). Satisfactory yields of 2, comparable with those of the Sandmeyer reaction, are obtained when X= 3-or 4-CF3, 2-, 3-, or 4-CN, 4-F, 4-MeO, 3-MeCO, 4-NO2, ...

 Related Synthetic Route
(4-bromophenyl)-phenylsulfanyldiazene Structure

52599-10-7

(4-bromophenyl)...

~3%

Terephthalonitrile Structure

623-26-7

Terephthalonitrile

1,4-bis(phenylsulfanyl)benzene Structure

3459-94-7

1,4-bis(phenyls...

4-Bromophenyl phenyl sulfide Structure

65662-88-6

4-Bromophenyl p...

Detail
(4-bromophenyl)-phenylsulfanyldiazene Structure

52599-10-7

(4-bromophenyl)...

Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

~3%

Terephthalonitrile Structure

623-26-7

Terephthalonitrile

1,4-bis(phenylsulfanyl)benzene Structure

3459-94-7

1,4-bis(phenyls...

Detail
phenyl(4-((phenylthio)diazenyl)phenyl)methanone Structure

111278-46-7

phenyl(4-((phen...

~40%

Benzophenone Structure

119-61-9

Benzophenone

phenyl-(4-phenylsulfanylphenyl)methanone Structure

6317-78-8

phenyl-(4-pheny...

4-Benzoylbenzonitrile Structure

1503-49-7

4-Benzoylbenzon...

phenyl(4-((phenylthio)diazenyl)phenyl)methanone Structure

111278-46-7

phenyl(4-((phen...

Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

~20%

Benzophenone Structure

119-61-9

Benzophenone

phenyl-(4-phenylsulfanylphenyl)methanone Structure

6317-78-8

phenyl-(4-pheny...

Detail
4-(phenylsulfanyldiazenyl)benzonitrile Structure

111278-47-8

4-(phenylsulfan...

Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

~19%

Terephthalonitrile Structure

623-26-7

Terephthalonitrile

phenyl-(4-phenylsulfanylphenyl)methanone Structure

6317-78-8

phenyl-(4-pheny...

N/A Structure

114650-60-1

N/A

~4%

Isophthalonitrile Structure

626-17-5

Isophthalonitrile

1,3-Bis(phenylthio)benzene Structure

2974-10-9

1,3-Bis(phenylt...

(3-bromophenyl)(phenyl)sulfane Structure

52089-10-8

(3-bromophenyl)...

Detail
Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

N/A Structure

114650-60-1

N/A

~4%

Isophthalonitrile Structure

626-17-5

Isophthalonitrile

1,3-Bis(phenylthio)benzene Structure

2974-10-9

1,3-Bis(phenylt...

Detail
(3-Methoxyphenyl)diazo phenyl sulfide Structure

114650-57-6

(3-Methoxypheny...

~21%

3-Methoxybenzonitrile Structure

1527-89-5

3-Methoxybenzon...

1-METHOXY-3-PHENYLSULFANYL-BENZENE Structure

30723-54-7

1-METHOXY-3-PHE...

Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

(3-Methoxyphenyl)diazo phenyl sulfide Structure

114650-57-6

(3-Methoxypheny...

~21%

3-Methoxybenzonitrile Structure

1527-89-5

3-Methoxybenzon...

1-METHOXY-3-PHENYLSULFANYL-BENZENE Structure

30723-54-7

1-METHOXY-3-PHE...

1-(phenylthio)-2-(3-(trifluoromethyl)phenyl)diazene Structure

114650-56-5

1-(phenylthio)-...

~62%

3-(Trifluoromethyl)benzonitrile Structure

368-77-4

3-(Trifluoromet...

(3-trifluoromethyl-phenyl)-phenyl sulfide Structure

2715-07-3

(3-trifluoromet...

Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

1-(phenylthio)-2-(3-(trifluoromethyl)phenyl)diazene Structure

114650-56-5

1-(phenylthio)-...

~61%

3-(Trifluoromethyl)benzonitrile Structure

368-77-4

3-(Trifluoromet...

4-Trifluoromethyl diphenyl sulfide Structure

53451-90-4

4-Trifluorometh...

(phenylsulfanyl)(phenyl)diazene Structure

42401-63-8

(phenylsulfanyl...

~32%

Diphenylsulfid Structure

139-66-2

Diphenylsulfid

Benzonitrile Structure

100-47-0

Benzonitrile

3-((phenylthio)diazenyl)benzonitrile Structure

114650-55-4

3-((phenylthio)...

~16%

Isophthalonitrile Structure

626-17-5

Isophthalonitrile

3-phenylsulfanylbenzonitrile Structure

108697-88-7

3-phenylsulfany...

N/A Structure

114650-60-1

N/A

~25%

Isophthalonitrile Structure

626-17-5

Isophthalonitrile

1,3-Bis(phenylthio)benzene Structure

2974-10-9

1,3-Bis(phenylt...

(3-bromophenyl)(phenyl)sulfane Structure

52089-10-8

(3-bromophenyl)...

Detail
Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

N/A Structure

114650-60-1

N/A

~20%

Isophthalonitrile Structure

626-17-5

Isophthalonitrile

1,3-Bis(phenylthio)benzene Structure

2974-10-9

1,3-Bis(phenylt...

Detail
Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

3-((phenylthio)diazenyl)benzonitrile Structure

114650-55-4

3-((phenylthio)...

~16%

Isophthalonitrile Structure

626-17-5

Isophthalonitrile

3-phenylsulfanylbenzonitrile Structure

108697-88-7

3-phenylsulfany...

(4-bromophenyl)-phenylsulfanyldiazene Structure

52599-10-7

(4-bromophenyl)...

Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

~7%

Terephthalonitrile Structure

623-26-7

Terephthalonitrile

1,4-bis(phenylsulfanyl)benzene Structure

3459-94-7

1,4-bis(phenyls...

Detail
4-(phenylsulfanyldiazenyl)benzonitrile Structure

111278-47-8

4-(phenylsulfan...

~38%

Terephthalonitrile Structure

623-26-7

Terephthalonitrile

4-phenylsulfanylbenzonitrile Structure

51238-46-1

4-phenylsulfany...

(4-bromophenyl)-phenylsulfanyldiazene Structure

52599-10-7

(4-bromophenyl)...

~15%

Terephthalonitrile Structure

623-26-7

Terephthalonitrile

1,4-bis(phenylsulfanyl)benzene Structure

3459-94-7

1,4-bis(phenyls...

4-Bromophenyl phenyl sulfide Structure

65662-88-6

4-Bromophenyl p...

Detail
(4-bromophenyl)-phenylsulfanyldiazene Structure

52599-10-7

(4-bromophenyl)...

Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

~14%

Terephthalonitrile Structure

623-26-7

Terephthalonitrile

1,4-bis(phenylsulfanyl)benzene Structure

3459-94-7

1,4-bis(phenyls...

Detail
(4-bromophenyl)-phenylsulfanyldiazene Structure

52599-10-7

(4-bromophenyl)...

Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

~15%

Terephthalonitrile Structure

623-26-7

Terephthalonitrile

1,4-bis(phenylsulfanyl)benzene Structure

3459-94-7

1,4-bis(phenyls...

Detail
1-(4-(phenylsulfonyl)phenyl)-2-(phenylthio)diazene Structure

111278-48-9

1-(4-(phenylsul...

~75%

Diphenyl sulfone Structure

127-63-9

Diphenyl sulfone

4-(phenylthio)diphenylsulfone Structure

32846-68-7

4-(phenylthio)d...

4-(Phenylsulfonyl)benzonitrile Structure

28525-13-5

4-(Phenylsulfon...

Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

1-(4-(phenylsulfonyl)phenyl)-2-(phenylthio)diazene Structure

111278-48-9

1-(4-(phenylsul...

~71%

Diphenyl sulfone Structure

127-63-9

Diphenyl sulfone

4-(phenylthio)diphenylsulfone Structure

32846-68-7

4-(phenylthio)d...

Detail
2-((phenylthio)diazenyl)benzonitrile Structure

114650-54-3

2-((phenylthio)...

~13%

2-phenylsulfanylbenzonitrile Structure

91804-55-6

2-phenylsulfany...

Phthalonitrile Structure

91-15-6

Phthalonitrile

Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

2-((phenylthio)diazenyl)benzonitrile Structure

114650-54-3

2-((phenylthio)...

~13%

2-phenylsulfanylbenzonitrile Structure

91804-55-6

2-phenylsulfany...

Phthalonitrile Structure

91-15-6

Phthalonitrile

(p-Methoxy-phenyldiazo)-phenyl-sulfid Structure

114650-58-7

(p-Methoxy-phen...

~19%

Benzene,1-methoxy-4-(phenylthio)- Structure

5633-57-8

Benzene,1-metho...

4-Methoxybenzonitrile Structure

874-90-8

4-Methoxybenzon...

(p-Methoxy-phenyldiazo)-phenyl-sulfid Structure

114650-58-7

(p-Methoxy-phen...

Tetrabutylammonium cyanide Structure

10442-39-4

Tetrabutylammon...

~19%

Benzene,1-methoxy-4-(phenylthio)- Structure

5633-57-8

Benzene,1-metho...

4-Methoxybenzonitrile Structure

874-90-8

4-Methoxybenzon...


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