55949-76-3

Basic information

• Product Name: Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester
• Synonyms: Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester
• CAS NO: 55949-76-3
• Molecular Weight: 182.176
• Mol File: 55949-76-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester(55949-76-3)
• EPA Substance Registry System: Cyclopenta-2,5-diene-1,2-dicarboxylic acid dimethyl ester(55949-76-3)

Safety Data

• Hazardous Substances Data: 55949-76-3(Hazardous Substances Data)

Upstream product

• 947-57-9 dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate 
• 2574-03-0 p-nitrobenzonitrile oxide 
• 622-37-7 Phenyl azide 
• 15500-73-9 4-methoxybenzonitrile oxide 
• 2101-87-3 p-methoxy-phenylazide 
• 873-67-6 benzonitrile oxide 
• 1516-60-5 4-nitrophenyl azide 
• 231289-36-4 C,N-Diphenylnitrilimine 

Relevant articles and documents

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

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.