Tetrahedron

Photochemical reaction of 1-and 2-naphthalenecarbonitrile with some methylbenzenes

A Albini, S Spreti

Index: Albini, Angelo; Spreti, Silvia Tetrahedron, 1984 , vol. 40, # 15 p. 2975 - 2982

Full Text: HTML

Citation Number: 18

Abstract

1-and 2-Naphthalenecarbonitriles (1-and 2-NN) photochemically react with 1, 2, 4, 5,- tetramethylbenzene (4)(but not with lower homologues). The products are 1, 1'-(1, 2-ethane- diyl) bis-(2, 4, 5-trimethylbenzene)(5) and 3-hydroxy-1-naphthalenecarbontrile with 1-NN and 5 and 1, 2-dihydro-2-naphthalenecarbonitrile with 2-NN. The reaction involves electron transfer to the NN singlet excited state followed by proton transfer. 4-Methylbenzyl-(1- ...

 Related Synthetic Route
2-Naphthonitrile Structure

613-46-7

2-Naphthonitrile

~5%

Benzene,1,1'-(1,2-ethanediyl)bis[4-methoxy- Structure

1657-55-2

Benzene,1,1'-(1...

1,2,3,4-tetrahydronaphthalene-2-carbonitrile Structure

51849-33-3

1,2,3,4-tetrahy...

1,2-dihydronaphthalene-2-carbonitrile Structure

20209-31-8

1,2-dihydronaph...

Detail
2-Naphthonitrile Structure

613-46-7

2-Naphthonitrile

~46%

1,2-dihydronaphthalene-2-carbonitrile Structure

20209-31-8

1,2-dihydronaph...

1,2,4-trimethyl-5-[2-(2,4,5-trimethylphenyl)ethyl]benzene Structure

18779-88-9

1,2,4-trimethyl...

2-Naphthonitrile Structure

613-46-7

2-Naphthonitrile

~37%

Benzene,1,1'-(1,2-ethanediyl)bis[4-methoxy- Structure

1657-55-2

Benzene,1,1'-(1...

1,2,3,4-tetrahydronaphthalene-2-carbonitrile Structure

51849-33-3

1,2,3,4-tetrahy...

1,2-dihydronaphthalene-2-carbonitrile Structure

20209-31-8

1,2-dihydronaph...

Detail
4-Methylanisole Structure

104-93-8

4-Methylanisole

2-Naphthonitrile Structure

613-46-7

2-Naphthonitrile

~38%

Benzene,1,1'-(1,2-ethanediyl)bis[4-methoxy- Structure

1657-55-2

Benzene,1,1'-(1...

1,2-dihydronaphthalene-2-carbonitrile Structure

20209-31-8

1,2-dihydronaph...

Detail
4-Methylanisole Structure

104-93-8

4-Methylanisole

2-Naphthonitrile Structure

613-46-7

2-Naphthonitrile

~38%

Benzene,1,1'-(1,2-ethanediyl)bis[4-methoxy- Structure

1657-55-2

Benzene,1,1'-(1...

1,2-dihydronaphthalene-2-carbonitrile Structure

20209-31-8

1,2-dihydronaph...

Detail
4-Methylanisole Structure

104-93-8

4-Methylanisole

~49%

Benzene,1,1'-(1,2-ethanediyl)bis[4-methoxy- Structure

1657-55-2

Benzene,1,1'-(1...

N/A Structure

94719-63-8

N/A

N/A Structure

94719-61-6

N/A

Detail
2-Naphthonitrile Structure

613-46-7

2-Naphthonitrile

~0%

Benzene,1,1'-(1,2-ethanediyl)bis[4-methoxy- Structure

1657-55-2

Benzene,1,1'-(1...

1,2,3,4-tetrahydronaphthalene-2-carbonitrile Structure

51849-33-3

1,2,3,4-tetrahy...

1,2-dihydronaphthalene-2-carbonitrile Structure

20209-31-8

1,2-dihydronaph...

Detail
4-Methylanisole Structure

104-93-8

4-Methylanisole

1-Cyanonaphthalene Structure

86-53-3

1-Cyanonaphthalene

~50%

Benzene,1,1'-(1,2-ethanediyl)bis[4-methoxy- Structure

1657-55-2

Benzene,1,1'-(1...

N/A Structure

94719-63-8

N/A

Detail
4-Methylanisole Structure

104-93-8

4-Methylanisole

2-Naphthonitrile Structure

613-46-7

2-Naphthonitrile

~0%

Benzene,1,1'-(1,2-ethanediyl)bis[4-methoxy- Structure

1657-55-2

Benzene,1,1'-(1...

1,2-dihydronaphthalene-2-carbonitrile Structure

20209-31-8

1,2-dihydronaph...

Detail
4-Methylanisole Structure

104-93-8

4-Methylanisole

2-Naphthonitrile Structure

613-46-7

2-Naphthonitrile

~0%

Benzene,1,1'-(1,2-ethanediyl)bis[4-methoxy- Structure

1657-55-2

Benzene,1,1'-(1...

1,2-dihydronaphthalene-2-carbonitrile Structure

20209-31-8

1,2-dihydronaph...

Detail
2-Naphthonitrile Structure

613-46-7

2-Naphthonitrile

~82%

1,2-dihydronaphthalene-2-carbonitrile Structure

20209-31-8

1,2-dihydronaph...

1,2,4-trimethyl-5-[2-(2,4,5-trimethylphenyl)ethyl]benzene Structure

18779-88-9

1,2,4-trimethyl...


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