85803-90-3

Basic information

• Product Name: exo-4-phenylbenzobicyclo<3.1.0>hex-2-ene
• Synonyms: exo-4-phenylbenzobicyclo<3.1.0>hex-2-ene
• CAS NO: 85803-90-3
• Molecular Weight: 206.287
• Mol File: 85803-90-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: exo-4-phenylbenzobicyclo<3.1.0>hex-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: exo-4-phenylbenzobicyclo<3.1.0>hex-2-ene(85803-90-3)
• EPA Substance Registry System: exo-4-phenylbenzobicyclo<3.1.0>hex-2-ene(85803-90-3)

Safety Data

• Hazardous Substances Data: 85803-90-3(Hazardous Substances Data)

Upstream product

• 16618-72-7 3-phenyl-1-indanone 
• 75-11-6 diiodomethane 
• 16606-46-5 1-phenyl-1,2-dihydronaphtalene 
• 67-56-1 methanol 

Downstream Products

• 605-02-7 1-phenylnaphthalene 
• 58719-65-6 (E)-1-styryl-2-vinylbenzene 
• 16606-46-5 1-phenyl-1,2-dihydronaphtalene 
• 13387-49-0 1-phenyl-1,4-dihydronaphthalene 
• 132884-12-9 (1S,αS;1R,αR)-1-(α-methoxybenzyl)indan 
• 132884-12-9 (1R,αS;1S,αR)-1-(α-methoxybenzyl)indan 
• 59154-50-6 cis-2-vinylstilbene 
• 20669-52-7 3-phenyl-1,2-dihydronaphthalene 
• 62019-39-0 2-phenyl-1,2-dihydronaphthalene 
• 7469-40-1 1-phenyl-3,4-dihydronaphthalene 

Relevant articles and documents

Photochemistry of 1-Phenyl-1,2-dihydronaphthalene in Methanol

The photochemistry of 1-phenyl-1,2-dihydronaphthalene (1) in methanol and hexane has been investigated.The lack of influence of solvent polarity and of the presence of sulfuric acid on the rate of formation of exo-4-phenylbenzobicyclohex-2-ene (exo-2) from the primary, ring-opened photoproduct cZt-3a of 1 precludes a sudden-polarized, zwitterionic excited state from being involved in the intramolecular photocycloaddition reaction leading to exo-2.The experimental results can be rationalized by assuming that this photoprocess involves a concerted ?4a+ ?2a-type electrocyclic reaction. cis-Dibenzobicycloocta-2,7-diene (8) is proposed to arise by photocyclization of cZc-3b, followed by a thermal rearrangement.On irradiation of 1 with a broad-spectrum lamp, the ratio of the photoproducts exo-2 and 8 is correlated with the ratio of the pe and pa conformers of 1.The novel compound 1-(o-benzylphenyl)allene (6) is also formed under these conditions.Irradiation of 1 at 254 nm yields 8 as the only photoproduct.Photochemical addition of methanol was observed to complete with the photoprocess, leading to exo-2, though at a comparatively low level.A photodecomposition mode of exo-2, presumably involving heterolytic cleavage of the cyclopropane ring, presents the chief source of methoxylated photoproducts at low temperatures in methanol.

Photochemistry of Phenyl-Substituted Benzobicyclohex-2-enes. A Reverse Di-?-methane Rearrangement

The photochemical rearrangements of phenyl-substituted benzobicyclohex-2-enes can generally be explained by assuming that homolytic fission of that cyclopropane bond which leads to the most stable diradical is the primary step.The final products are formed by 1,2 hydrogen shifts in the intermediate.An exception to this general pattern was observed with 5-phenylbenzobicyclohex-2-ene (5).The photoproducts of 5 could only be explained by assuming reverse di-?-methane rearrangements followed by 1,3 hydrogen shifts.It is argued that this reaction path is followed because of the high rate to the back-reaction of the homolytic bond fission of 5.