Proton Mobility in 2??Substituted 1, 3??Dichlorobenzenes:“ortho” or “meta” Metalation?

M Schlosser, C Heiss, E Marzi…

Index: Schlosser, Manfred; Heiss, Christophe; Marzi, Elena; Scopelliti, Rosario European Journal of Organic Chemistry, 2006 , # 19 p. 4398 - 4404

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Citation Number: 9

Abstract

Abstract Nine 1, 3-dichlorobenzene congeners were selected as model compounds to assess the relative rates of proton abstraction from 4-and 5-positions (“ortho” vs.“meta” metalation). Using lithium 2, 2, 6, 6-tetramethylpiperidide as the basic reagent, the chlorine- adjacent 4-position underwent metalation exclusively. In contrast, attack at the chlorine- remote 5-position became significant even in the case of moderately sized 2-substituents ( ...

 Related Synthetic Route
Carbon dioxide Structure

124-38-9

Carbon dioxide

1,2,3-trichlorobenzene Structure

87-61-6

1,2,3-trichloro...

~88%

trichlorobenzoic acid Structure

50-75-9

trichlorobenzoi...

Learn More
Carbon dioxide Structure

124-38-9

Carbon dioxide

1,2,3-trichlorobenzene Structure

87-61-6

1,2,3-trichloro...

~65%

trichlorobenzoic acid Structure

50-75-9

trichlorobenzoi...

2,3-Dichlorobenzoic acid Structure

50-45-3

2,3-Dichloroben...

Detail Learn More
Carbon dioxide Structure

124-38-9

Carbon dioxide

1,3-dichloro-5-iodo--2-methylbenzene Structure

177167-52-1

1,3-dichloro-5-...

~91%

3,5-Dichloro-4-methylbenzoic acid Structure

39652-34-1

3,5-Dichloro-4-...

Learn More
Carbon dioxide Structure

124-38-9

Carbon dioxide

2,6-Dichlorotoluene Structure

118-69-4

2,6-Dichlorotoluene

~%

2,6-Dichlorophenylacetic acid Structure

6575-24-2

2,6-Dichlorophe...

3,5-Dichloro-4-methylbenzoic acid Structure

39652-34-1

3,5-Dichloro-4-...

Detail Learn More
1,3-Dichloro-5-iodobenzene Structure

3032-81-3

1,3-Dichloro-5-...

~%

3,5-Dichloro-4-methylbenzoic acid Structure

39652-34-1

3,5-Dichloro-4-...

Learn More
1,5-dibromo-2,3,4-trichlorobenzene Structure

811720-26-0

1,5-dibromo-2,3...

~%

5-Bromo-1,2,3-trichlorobenzene Structure

21928-51-8

5-Bromo-1,2,3-t...

1-Bromo-2,3,4-trichlorobenzene Structure

81067-37-0

1-Bromo-2,3,4-t...

Learn More
N/A Structure

915144-97-7

N/A

~%

1-Bromo-2,3,4-trichlorobenzene Structure

81067-37-0

1-Bromo-2,3,4-t...

Learn More
N/A Structure

915144-98-8

N/A

~%

1-Bromo-2,3,4-trichlorobenzene Structure

81067-37-0

1-Bromo-2,3,4-t...

Learn More
1,3-Dichlorobenzene Structure

541-73-1

1,3-Dichlorobenzene

~99%

1,3-Dichloro-2-iodobenzene Structure

19230-28-5

1,3-Dichloro-2-...

Learn More
1,5-dibromo-2,3,4-trichlorobenzene Structure

811720-26-0

1,5-dibromo-2,3...

~48%

5-Bromo-1,2,3-trichlorobenzene Structure

21928-51-8

5-Bromo-1,2,3-t...

Learn More
Carbon dioxide Structure

124-38-9

Carbon dioxide

1,2,3-trichlorobenzene Structure

87-61-6

1,2,3-trichloro...

~13%

trichlorobenzoic acid Structure

50-75-9

trichlorobenzoi...

2,3-Dichlorobenzoic acid Structure

50-45-3

2,3-Dichloroben...

Detail Learn More
Carbon dioxide Structure

124-38-9

Carbon dioxide

1,2,3-trichlorobenzene Structure

87-61-6

1,2,3-trichloro...

~6%

trichlorobenzoic acid Structure

50-75-9

trichlorobenzoi...

2,3-Dichlorobenzoic acid Structure

50-45-3

2,3-Dichloroben...

Detail Learn More
Carbon dioxide Structure

124-38-9

Carbon dioxide

5-Bromo-1,2,3-trichlorobenzene Structure

21928-51-8

5-Bromo-1,2,3-t...

~%

3,4,5-Trichlorobenzoic acid Structure

51-39-8

3,4,5-Trichloro...

Learn More
1,5-dibromo-2,3,4-trichlorobenzene Structure

811720-26-0

1,5-dibromo-2,3...

~%

3,4,5-Trichlorobenzoic acid Structure

51-39-8

3,4,5-Trichloro...

Learn More
N/A Structure

915144-97-7

N/A

~%

3,4,5-Trichlorobenzoic acid Structure

51-39-8

3,4,5-Trichloro...

Learn More
N/A Structure

915144-98-8

N/A

~%

3,4,5-Trichlorobenzoic acid Structure

51-39-8

3,4,5-Trichloro...

Learn More
1,3-Dichloro-2-iodobenzene Structure

19230-28-5

1,3-Dichloro-2-...

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

~67%

1,3-Dichloro-2-(trifluoromethyl)benzene Structure

104359-35-5

1,3-Dichloro-2-...

Learn More
Diethyl sulfate Structure

64-67-5

Diethyl sulfate

1,3-Dichlorobenzene Structure

541-73-1

1,3-Dichlorobenzene

~89%

1,3-dichloro-2-ethylbenzene Structure

33407-02-2

1,3-dichloro-2-...

Learn More
Carbon dioxide Structure

124-38-9

Carbon dioxide

1,2-Dichlorobenzene Structure

95-50-1

1,2-Dichlorobenzene

~87%

2,3-Dichlorobenzoic acid Structure

50-45-3

2,3-Dichloroben...

Learn More
Carbon dioxide Structure

124-38-9

Carbon dioxide

2,6-Dichlorotoluene Structure

118-69-4

2,6-Dichlorotoluene

~%

2,6-Dichlorophenylacetic acid Structure

6575-24-2

2,6-Dichlorophe...

3,5-Dichloro-4-methylbenzoic acid Structure

39652-34-1

3,5-Dichloro-4-...

Detail Learn More

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