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Tetrahedron

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

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

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

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被引用次数: 31

摘要

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, ...

(4-bromophenyl)-phenylsulfanyldiazene结构式

(4-bromophenyl)...

~3%

对苯二甲腈结构式

对苯二甲腈

1,4-bis(phenylsulfanyl)benzene结构式

1,4-bis(phenyls...

(4-溴苯基)(苯基)硫烷结构式

(4-溴苯基)(苯基)硫烷

详细

(4-bromophenyl)-phenylsulfanyldiazene结构式

(4-bromophenyl)...

氰化四丁基胺结构式

氰化四丁基胺

~3%

对苯二甲腈结构式

对苯二甲腈

1,4-bis(phenylsulfanyl)benzene结构式

1,4-bis(phenyls...

详细

phenyl(4-((phenylthio)diazenyl)phenyl)methanone结构式

phenyl(4-((phen...

~40%

二苯甲酮结构式

phenyl-(4-phenylsulfanylphenyl)methanone结构式

phenyl-(4-pheny...

4-苯甲酰基苯腈结构式

4-苯甲酰基苯腈

phenyl(4-((phenylthio)diazenyl)phenyl)methanone结构式

phenyl(4-((phen...

氰化四丁基胺结构式

氰化四丁基胺

~20%

二苯甲酮结构式

phenyl-(4-phenylsulfanylphenyl)methanone结构式

phenyl-(4-pheny...

详细

4-(phenylsulfanyldiazenyl)benzonitrile结构式

4-(phenylsulfan...

氰化四丁基胺结构式

氰化四丁基胺

~19%

对苯二甲腈结构式

对苯二甲腈

phenyl-(4-phenylsulfanylphenyl)methanone结构式

phenyl-(4-pheny...

未登录结构式

~4%

间苯二甲腈结构式

间苯二甲腈

1,3-Bis(phenylthio)benzene结构式

1,3-Bis(phenylt...

(3-bromophenyl)(phenyl)sulfane结构式

(3-bromophenyl)...

详细

氰化四丁基胺结构式

氰化四丁基胺

未登录结构式

~4%

间苯二甲腈结构式

间苯二甲腈

1,3-Bis(phenylthio)benzene结构式

1,3-Bis(phenylt...

详细

(3-Methoxyphenyl)diazo phenyl sulfide结构式

(3-Methoxypheny...

~21%

3-甲氧基苯腈结构式

3-甲氧基苯腈

1-甲氧基-3-苯磺酰基苯结构式

1-甲氧基-3-苯磺酰基苯

氰化四丁基胺结构式

氰化四丁基胺

(3-Methoxyphenyl)diazo phenyl sulfide结构式

(3-Methoxypheny...

~21%

3-甲氧基苯腈结构式

3-甲氧基苯腈

1-甲氧基-3-苯磺酰基苯结构式

1-甲氧基-3-苯磺酰基苯

1-(phenylthio)-2-(3-(trifluoromethyl)phenyl)diazene结构式

1-(phenylthio)-...

~62%

间三氟甲基苯腈结构式

间三氟甲基苯腈

(3-trifluoromethyl-phenyl)-phenyl sulfide结构式

(3-trifluoromet...

氰化四丁基胺结构式

氰化四丁基胺

1-(phenylthio)-2-(3-(trifluoromethyl)phenyl)diazene结构式

1-(phenylthio)-...

~61%

间三氟甲基苯腈结构式

间三氟甲基苯腈

4-三氟甲基二苯硫醚结构式

4-三氟甲基二苯硫醚

(phenylsulfanyl)(phenyl)diazene结构式

(phenylsulfanyl...

~32%

苯硫醚结构式

苯甲腈结构式

3-((phenylthio)diazenyl)benzonitrile结构式

3-((phenylthio)...

~16%

间苯二甲腈结构式

间苯二甲腈

3-phenylsulfanylbenzonitrile结构式

3-phenylsulfany...

未登录结构式

~25%

间苯二甲腈结构式

间苯二甲腈

1,3-Bis(phenylthio)benzene结构式

1,3-Bis(phenylt...

(3-bromophenyl)(phenyl)sulfane结构式

(3-bromophenyl)...

详细

氰化四丁基胺结构式

氰化四丁基胺

未登录结构式

~20%

间苯二甲腈结构式

间苯二甲腈

1,3-Bis(phenylthio)benzene结构式

1,3-Bis(phenylt...

详细

氰化四丁基胺结构式

氰化四丁基胺

3-((phenylthio)diazenyl)benzonitrile结构式

3-((phenylthio)...

~16%

间苯二甲腈结构式

间苯二甲腈

3-phenylsulfanylbenzonitrile结构式

3-phenylsulfany...

(4-bromophenyl)-phenylsulfanyldiazene结构式

(4-bromophenyl)...

氰化四丁基胺结构式

氰化四丁基胺

~7%

对苯二甲腈结构式

对苯二甲腈

1,4-bis(phenylsulfanyl)benzene结构式

1,4-bis(phenyls...

详细

4-(phenylsulfanyldiazenyl)benzonitrile结构式

4-(phenylsulfan...

~38%

对苯二甲腈结构式

对苯二甲腈

4-phenylsulfanylbenzonitrile结构式

4-phenylsulfany...

(4-bromophenyl)-phenylsulfanyldiazene结构式

(4-bromophenyl)...

~15%

对苯二甲腈结构式

对苯二甲腈

1,4-bis(phenylsulfanyl)benzene结构式

1,4-bis(phenyls...

(4-溴苯基)(苯基)硫烷结构式

(4-溴苯基)(苯基)硫烷

详细

(4-bromophenyl)-phenylsulfanyldiazene结构式

(4-bromophenyl)...

氰化四丁基胺结构式

氰化四丁基胺

~14%

对苯二甲腈结构式

对苯二甲腈

1,4-bis(phenylsulfanyl)benzene结构式

1,4-bis(phenyls...

详细

(4-bromophenyl)-phenylsulfanyldiazene结构式

(4-bromophenyl)...

氰化四丁基胺结构式

氰化四丁基胺

~15%

对苯二甲腈结构式

对苯二甲腈

1,4-bis(phenylsulfanyl)benzene结构式

1,4-bis(phenyls...

详细

1-(4-(phenylsulfonyl)phenyl)-2-(phenylthio)diazene结构式

1-(4-(phenylsul...

~75%

二苯砜结构式

4-(phenylthio)diphenylsulfone结构式

4-(phenylthio)d...

4-(苯磺酰基)苯腈结构式

4-(苯磺酰基)苯腈

氰化四丁基胺结构式

氰化四丁基胺

1-(4-(phenylsulfonyl)phenyl)-2-(phenylthio)diazene结构式

1-(4-(phenylsul...

~71%

二苯砜结构式

4-(phenylthio)diphenylsulfone结构式

4-(phenylthio)d...

详细

2-((phenylthio)diazenyl)benzonitrile结构式

2-((phenylthio)...

~13%

2-phenylsulfanylbenzonitrile结构式

2-phenylsulfany...

邻苯二甲腈结构式

邻苯二甲腈

氰化四丁基胺结构式

氰化四丁基胺

2-((phenylthio)diazenyl)benzonitrile结构式

2-((phenylthio)...

~13%

2-phenylsulfanylbenzonitrile结构式

2-phenylsulfany...

邻苯二甲腈结构式

邻苯二甲腈

(p-Methoxy-phenyldiazo)-phenyl-sulfid结构式

(p-Methoxy-phen...

~19%

Benzene,1-methoxy-4-(phenylthio)-结构式

Benzene,1-metho...

4-甲氧基苯甲腈结构式

4-甲氧基苯甲腈

(p-Methoxy-phenyldiazo)-phenyl-sulfid结构式

(p-Methoxy-phen...

氰化四丁基胺结构式

氰化四丁基胺

~19%

Benzene,1-methoxy-4-(phenylthio)-结构式

Benzene,1-metho...

4-甲氧基苯甲腈结构式

4-甲氧基苯甲腈

Magnesium-induced copper-catalyzed synthesis of unsymmetrica...

[Taniguchi, Nobukazu; Onami, Tetsuo Journal of Organic Chemistry, 2004 , vol. 69, # 3 p. 915 - 920]

A convenient s rn 1 synthesis of aromatic nitriles from diaz...

[Tetrahedron, , vol. 43, # 20 p. 4625 - 4634]

A mild and efficient SRN1 approach to diaryl sulfides from a...

[Petrillo, Giovanni; Novi, Marino; Garbarino, Giacomo; Dell'Erba, Carlo Tetrahedron, 1986 , vol. 42, # 14 p. 4007 - 4016]

A mild and efficient SRN1 approach to diaryl sulfides from a...

[Petrillo, Giovanni; Novi, Marino; Garbarino, Giacomo; Dell'Erba, Carlo Tetrahedron, 1986 , vol. 42, # 14 p. 4007 - 4016]

A mild and efficient SRN1 approach to diaryl sulfides from a...

[Petrillo, Giovanni; Novi, Marino; Garbarino, Giacomo; Dell'Erba, Carlo Tetrahedron, 1986 , vol. 42, # 14 p. 4007 - 4016]