On the mechanism of disproportionation reactions of 1, 2-dihydroquinolines

TP Forrest, GA Dauphinee…

Index: Forrest, T. P.; Dauphinee, G. A.; Deraniyagala, S. A. Canadian Journal of Chemistry, 1985 , vol. 63, p. 412 - 417

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Citation Number: 35

Abstract

The commonly accepted mechanism for the acid-catalyzed disproportionation of 1, 2- dihydroquinolines involves a hydride transfer from C-2 of one dihydroquinoline molecule to C-4 of another molecule which has already been protonated at C-3. This mechanism is shown to be incorrect. The proposed intermediate is shown to react by solvent addition and not by reduction under the conditions of the reaction. Evidence has been obtained which ...

 Related Synthetic Route
1,2-dihydroquinoline Structure

612-18-0

1,2-dihydroquinoline

~%

2-Pphenyl-1,2,3,4-tetrahydroquinoline Structure

24005-23-0

2-Pphenyl-1,2,3...

leucoline Structure

91-22-5

leucoline

METHYLLITHIUM Structure

917-54-4

METHYLLITHIUM

~87%

2-methyl-1,2-dihydroquinoline Structure

1125-81-1

2-methyl-1,2-di...

1,2-dihydroquinoline Structure

612-18-0

1,2-dihydroquinoline

~%

2-methyl-1,2-dihydroquinoline Structure

1125-81-1

2-methyl-1,2-di...

1,2-dihydroquinoline Structure

612-18-0

1,2-dihydroquinoline

~%

1,4-dihydroquinoline Structure

50624-35-6

1,4-dihydroquinoline

leucoline Structure

91-22-5

leucoline

~%

2-Pphenyl-1,2,3,4-tetrahydroquinoline Structure

24005-23-0

2-Pphenyl-1,2,3...

6-Methylquinoline Structure

91-62-3

6-Methylquinoline

~%

6-Methyl-2-phenylquinoline Structure

27356-46-3

6-Methyl-2-phen...

Phenyllithium Structure

591-51-5

Phenyllithium

~%

6-Methyl-2-phenylquinoline Structure

27356-46-3

6-Methyl-2-phen...

p-Toluidine Structure

106-49-0

p-Toluidine

~%

2,6-dimethyl-1,2,3,4-tetrahydroquinoline Structure

16078-45-8

2,6-dimethyl-1,...

2-methyl-1,2-dihydroquinoline Structure

1125-81-1

2-methyl-1,2-di...

trans 4-hydroxy-2,6-dimethyl-1,2,3,4-tetrahydroquinoline Structure

26344-24-1

trans 4-hydroxy...

~%

2,6-dimethyl-1,2,3,4-tetrahydroquinoline Structure

16078-45-8

2,6-dimethyl-1,...

2,6-dimethyl-1,2-dihydroquinoline Structure

46038-60-2

2,6-dimethyl-1,...

N/A Structure

97531-29-8

N/A

~%

2,6-dimethyl-1,2,3,4-tetrahydroquinoline Structure

16078-45-8

2,6-dimethyl-1,...

tetrahydroquinaldine Structure

1780-19-4

tetrahydroquinaldine


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