42577-15-1

Basic information

• Product Name: 3-Cyclobutene-1α,2α-dicarboxylic acid dimethyl ester
• Synonyms: 3-Cyclobutene-1,2-dicarboxylic acid, dimethyl ester, (1R,2S)-rel- (9CI)
• CAS NO: 42577-15-1
• Molecular Formula: C8H10O4
• Molecular Weight: 170.1626
• Mol File: 42577-15-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Cyclobutene-1α,2α-dicarboxylic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclobutene-1α,2α-dicarboxylic acid dimethyl ester(42577-15-1)
• EPA Substance Registry System: 3-Cyclobutene-1α,2α-dicarboxylic acid dimethyl ester(42577-15-1)

Safety Data

• Hazardous Substances Data: 42577-15-1(Hazardous Substances Data)

Upstream product

• 4933-63-5 1,2-dibromocyclobutene-cis-3,4-dicarboxylic acid 
• 10374-07-9 cyclobut-3-ene-1,2-dicarboxylic acid anhydride 
• 67-56-1 methanol 
• 10374-07-9 3-oxabicyclo<3.2.0>hept-6-ene-2,4-dione 
• 186581-53-3 diazomethane 
• 27652-29-5 cis-Cyclobut-1-en-3,4-dicarbonsaeure 
• 4933-64-6 1,2-dibromocyclobutene-cis-3,4-dicarboxylicdimethyl ester 

Downstream Products

• 151715-95-6 methyl hydrogen (1R,2S)-(+)-3-cyclobutene-1,2-dicarboxylate 
• 126036-80-4 (1S,4S,5S,6S,7S)-4-Phenyl-2,3-diaza-bicyclo[3.2.0]hept-2-ene-6,7-dicarboxylic acid dimethyl ester 
• 126108-26-7 (1S,4R,5S,6S,7S)-4-Phenyl-2,3-diaza-bicyclo[3.2.0]hept-2-ene-6,7-dicarboxylic acid dimethyl ester 
• 126108-40-5 (1S,4S,5S,6R,7R)-4-Phenyl-2,3-diaza-bicyclo[3.2.0]hept-2-ene-6,7-dicarboxylic acid dimethyl ester 

Relevant articles and documents

Modifying Woodward–Hoffmann Stereoselectivity Under Vibrational Strong Coupling

Vibrational strong coupling (VSC) has recently been shown to change the rate and chemoselectivity of ground-state chemical reactions via the formation of light–matter hybrid polaritonic states. However, the observation that vibrational-mode symmetry has a large influence on charge-transfer reactions under VSC suggests that symmetry considerations could be used to control other types of chemical selectivity through VSC. Here, we show that VSC influences the stereoselectivity of the thermal electrocyclic ring opening of a cyclobutene derivative, a reaction which follows the Woodward–Hoffmann rules. The direction of the change in stereoselectivity depends on the vibrational mode that is coupled, as do changes in rate and reaction thermodynamics. These results on pericyclic reactions confirm that symmetry plays a key role in chemistry under VSC.

Preparation and Pyrolysis of some Bi- and Tri-cyclic Sulfones Derived from Photochemical Cyacloaddition of 2,3-Dihydrothiophene 1,1-Dioxide (2-Sulfolene)

Photochemical reaction of 2,3-dihydrothiophene 1,1-dioxide with maleic anhydride gives the cycloadduct 8 and simple reactions of the anhydride function provide access to a wide range of new bi- and tri-cyclic sulfones 9-13 and 15-24 containing the novel 2-thiabicycloheptane 2,2-dioxide ring system.On pyrolysis these undergo either cycloreversion with elimination of 2-sulfolene or in one case extrusion of ethene and SO2 to give the 1,3-diene.Oxidative bis-decarboxylation of the diacid from hydrolysis of 8 gives the new simple alkene sulfone 31.Pyrolysis of this results in loss of only SO2 to give cyclohexa-1,3-diene, but its epoxide 34 loses SO2 and ethene to afford furan, thus making 31 a synthetic equivalent of cyclobutadiene.