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Cas Database

55949-76-3

55949-76-3

Identification

  • Product Name:Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester

  • CAS Number: 55949-76-3

  • EINECS:

  • Molecular Weight:182.176

  • Molecular Formula: C9H10O4

  • HS Code:

  • Mol File:55949-76-3.mol

Synonyms:Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester

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Relevant articles and documentsAll total 1 Articles be found

SITE SELECTIVITY IN THE REACTIONS OF 1,3-DIPOLES WITH NORBORNADIENE DERIVATIVES

Cristina, D.,Amici, M. De,Micheli, C. De,Gandolfi, R.

, p. 1349 - 1357 (2007/10/02)

The cycloadditions of arylazides, benzonitrile oxides and diphenylnitrile imine to norbornadiene derivatives 1a-c showed varying degree of site- and stereo-selectivity.With dipolarophile 1a arylazides and benzonitrile oxides attack, preferentially, the electron-poor tetrasubstituted double bond, while in the case of 1b and 1c is the substituted double bond which enters the cycloaddition.By contrast, 2-diazopropane and C-phenyl-N-methylnitrone react with the sole tetrasubstituted double bond of 1a-c in stereo- and site-specific cycloadditions.The quantitative evaluation of the two possible reaction paths was performed by glc analysis.The compounds detected were those arising from Diels-Alder cycloreversions of the thermally labile intermediate adducts 2 and 3 (Scheme 1).The results were rationalized on the basis of a qualitative perturbation treatment which considers frontier orbital interactions only.

Process route upstream and downstream products

Process route

4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate
947-57-9

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate

1-(4-nitrophenyl)-1H-1,2,3-triazole
1204-91-7

1-(4-nitrophenyl)-1H-1,2,3-triazole

1-(4-nitro-phenyl)-1<i>H</i>-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester
4999-94-4

1-(4-nitro-phenyl)-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester
55949-76-3

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
In benzene; Ambient temperature;
8.5 % Chromat.
91.5 % Chromat.
In benzene; for 24h; Heating;
91.5 % Chromat.
8.5 % Chromat.
dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate
947-57-9

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate

Phenyl azide
622-37-7

Phenyl azide

1-phenyl-1,2,3-triazole
1453-81-2

1-phenyl-1,2,3-triazole

1-phenyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester
17304-69-7

1-phenyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester
55949-76-3

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
In benzene; for 24h; Heating;
23.0 % Chromat.
77 % Chromat.
In benzene; for 24h; Heating;
77.0 % Chromat.
23.0 % Chromat.
benzonitrile oxide
873-67-6

benzonitrile oxide

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate
947-57-9

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate

3-phenylisoxazole
1006-65-1

3-phenylisoxazole

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester
55949-76-3

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester

dimethyl 3-phenylisoxazole-4,5-dicarboxylate
7710-44-3

dimethyl 3-phenylisoxazole-4,5-dicarboxylate

Conditions
Conditions Yield
In benzene; for 2h; Heating;
13.5 % Chromat.
86.5 % Chromat.
dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate
947-57-9

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate

p-methoxy-phenylazide
2101-87-3

p-methoxy-phenylazide

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester
55949-76-3

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester

1-(4-methoxyphenyl)-1H-[1,2,3]triazole
68535-49-9

1-(4-methoxyphenyl)-1H-[1,2,3]triazole

dimethyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4,5-dicarboxylate
4953-05-3

dimethyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4,5-dicarboxylate

Conditions
Conditions Yield
In benzene; for 24h; Heating;
22.5 % Chromat.
77.5 % Chromat.
dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate
947-57-9

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate

p-nitrobenzonitrile oxide
2574-03-0

p-nitrobenzonitrile oxide

3-(p-nitrophenyl)isoxazole
4264-05-5

3-(p-nitrophenyl)isoxazole

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester
55949-76-3

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester

3-(4-nitro-phenyl)-isoxazole-4,5-dicarboxylic acid dimethyl ester
53890-65-6

3-(4-nitro-phenyl)-isoxazole-4,5-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
In benzene; for 2h; Heating;
3.8 % Chromat.
96.2 % Chromat.
dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate
947-57-9

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate

C,N-Diphenylnitrilimine
231289-36-4

C,N-Diphenylnitrilimine

1,3-diphenyl-1H-pyrazole
4492-01-7

1,3-diphenyl-1H-pyrazole

dimethyl 1,3-diphenyl-1H-pyrazole-4,5-dicarboxylate
41555-25-3

dimethyl 1,3-diphenyl-1H-pyrazole-4,5-dicarboxylate

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester
55949-76-3

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
In benzene; Ambient temperature;
80.5 % Chromat.
19.5 % Chromat.
dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate
947-57-9

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate

4-methoxybenzonitrile oxide
15500-73-9

4-methoxybenzonitrile oxide

dimethyl 3-(4-methoxyphenyl)isoxazole-4,5-dicarboxylate
59291-70-2

dimethyl 3-(4-methoxyphenyl)isoxazole-4,5-dicarboxylate

3-(4-methoxyphenyl)isoxazole
61428-20-4

3-(4-methoxyphenyl)isoxazole

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester
55949-76-3

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
In benzene; for 2h; Heating;
89.4 % Chromat.
10.6 % Chromat.
In benzene; Product distribution; Ambient temperature; reaction of other dipolarophiles with different 1,3-dipoles, effect of solvent polarity;
10.6 % Chromat.
89.4 % Chromat.
4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate
947-57-9

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate

1-(4-nitrophenyl)-1H-1,2,3-triazole
1204-91-7

1-(4-nitrophenyl)-1H-1,2,3-triazole

1-(4-nitro-phenyl)-1<i>H</i>-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester
4999-94-4

1-(4-nitro-phenyl)-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester
55949-76-3

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
In benzene; Ambient temperature;
8.5 % Chromat.
91.5 % Chromat.
In benzene; for 24h; Heating;
91.5 % Chromat.
8.5 % Chromat.
dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate
947-57-9

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate

Phenyl azide
622-37-7

Phenyl azide

1-phenyl-1,2,3-triazole
1453-81-2

1-phenyl-1,2,3-triazole

1-phenyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester
17304-69-7

1-phenyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester
55949-76-3

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
In benzene; for 24h; Heating;
23.0 % Chromat.
77 % Chromat.
In benzene; for 24h; Heating;
77.0 % Chromat.
23.0 % Chromat.
benzonitrile oxide
873-67-6

benzonitrile oxide

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate
947-57-9

dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate

3-phenylisoxazole
1006-65-1

3-phenylisoxazole

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester
55949-76-3

Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester

dimethyl 3-phenylisoxazole-4,5-dicarboxylate
7710-44-3

dimethyl 3-phenylisoxazole-4,5-dicarboxylate

Conditions
Conditions Yield
In benzene; for 2h; Heating;
13.5 % Chromat.
86.5 % Chromat.

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