180578-72-7

Basic information

• Product Name: 2,3-bis(4-methylphenyl)bicyclo[2.2.2]oct-2-ene
• Synonyms: 2,3-bis(4-methylphenyl)bicyclo[2.2.2]oct-2-ene
• CAS NO: 180578-72-7
• Molecular Weight: 288.433
• Mol File: 180578-72-7.mol

Chemical Properties

• CAS DataBase Reference: 2,3-bis(4-methylphenyl)bicyclo[2.2.2]oct-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-bis(4-methylphenyl)bicyclo[2.2.2]oct-2-ene(180578-72-7)
• EPA Substance Registry System: 2,3-bis(4-methylphenyl)bicyclo[2.2.2]oct-2-ene(180578-72-7)

Safety Data

• Hazardous Substances Data: 180578-72-7(Hazardous Substances Data)

Upstream product

• 112439-97-1 2,3-dibromobicyclo(2.2.2)oct-2-ene 
• 4294-57-9 para-methylphenylmagnesium bromide 

Relevant articles and documents

Vicinal-diaryl interactions in stilbenoid hydrocarbons as observed in the through-space charge delocalization of their cation radicals

The conformational preference of vicinal or 1,2-phenyl groups is probed in two classes of ring-substituted 1,2-diphenylbicyclooctene (stilbenoid) hydrocarbons 1a-1d and 2a-2c. UV-vis spectroscopy reveals, and X-ray crystallography verifies, the intramolecular (edge-to-face) orientation for the phenyl-phenyl interaction in stilbenoids 1a-1d. Most importantly, when two pairs of ortho-methyl substituents are present, the cofacial phenyl groups in the stilbenoid donors are established by X-ray crystallography and spectrally observed in the cation radicals (2a+?-2c+?) by the appearance of new bands with strong absorptions in the near IR with λmax = 1100-1315 nm, analogous to those previously observed in intermolecular (aromatic) interactions of aromatic cation radicals.

Efficient hydrogenation of sterically hindered olefins with borane-methyl sulfide complex

Sterically hindered olefins are efficiently reduced to the corresponding alkanes by the boranemethyl sulfide (BMS) complex at room temperature (or below) in dichloromethane containing a mild one-electron oxidant (such as an aromatic cation radical) or by the passage of an anodic current. In an alternative procedure, the hydrogenation of the same (electron-rich) olefins with the BMS complex (in the absence of a one-electron oxidant) is also carried out in the presence of a strong Bronsted acid (such as HBF4). In the oxidative activation, olefin cation radicals are the first observable intermediates, and separate experiments (including transient electrochemistry) confirm the facile reduction of the olefin cation radical by borane to produce the corresponding alkane. The direct protonation of olefins produces carbocationic intermediates which are also efficiently reduced by borane to the corresponding alkanes. The intermediacy of both olefin cation radicals and carbocations in the hydrogenation procedure with borane is discussed.