4237-08-5

Basic information

• Product Name: 2-Phenylnorborna-2-ene
• Synonyms: 2-Phenylbicyclo[2.2.1]hept-2-ene;2-Phenylnorborna-2-ene
• CAS NO: 4237-08-5
• Molecular Formula: C₁₃H₁₄
• Molecular Weight: 170.25
• Mol File: 4237-08-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Phenylnorborna-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenylnorborna-2-ene(4237-08-5)
• EPA Substance Registry System: 2-Phenylnorborna-2-ene(4237-08-5)

Safety Data

• Hazardous Substances Data: 4237-08-5(Hazardous Substances Data)

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 3604-36-2 methyl bicyclo[2.2.1]hepta-2,5-diene-2-carboxylate 
• 109909-04-8 endo-2-phenyl-exo-3,4,5-trithiatricyclo<5.2.1.0^2,6>decane 
• 497-38-1 Norbornan-2-on 
• 591-51-5 phenyllithium 
• 591-50-4 iodobenzene 
• 694-90-6 2-bromobicyclo[2.2.1]hept-2-ene 
• 503275-67-0 2-bromo-3-deuterobicyclo[2.2.1]hept-2-ene 
• 75267-72-0 2,3-dibromobicyclo[2.1.1]hept-2-ene 
• 128780-28-9 2,3-dibromobicyclo[2.2.1]hepta-2,5-diene 
• 498-66-8 norborn-2-ene 
• 6196-83-4 exo-2-phenyl-endo-bicyclo<2.2.1>heptan-2-ol 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 701-15-5 methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate 

Downstream Products

• 85267-40-9 N-(3-Phenyl-bicyclo[2.2.1]hept-2-yl)-acetamide 
• 85267-41-0 N-(3-Phenyl-tricyclo[2.2.1.0^2,6]hept-3-yl)-acetamide 
• 85267-39-6 3,3'-Diphenyl-[2,2']bi[bicyclo[2.2.1]heptyl]-2,2'-diene 
• 31062-80-3 endo-3-phenyl-2-norbornanone 
• 62226-45-3 endo-2-(4-bromophenyl)norbornane 
• 81675-46-9 endo-2-(<4-3H>phenyl)norbornane 
• 62226-44-2 endo-2-(2-bromophenyl)norbornane 

Relevant articles and documents

Palladium-catalyzed hydrophenylation of bicyclic alkenes

Palladium-catalyzed hydrophenylation reactions of bicyclic alkenes were investigated. These reactions were found to be completely chemo- and stereoselective, giving only exo products on the less substituted double bonds of bicyclic alkenes in moderate to good yields. For unsymmetrical bicyclic alkenes, regioselectivities of 52:48 to 100:0 were observed with various substituents on the bicyclic alkenes.

Solvolytic elimination reactions. Stepwise or concerted?

2-Aryl-endo-2-norbornyl trifluoroacetates 11 solvolyze to give a significant fraction of elimination product. A deuterium labeling study showed that the exo hydrogen is lost exclusively when the elimination product forms. A concerted ester pyrolysis type of mechanism is therefore ruled out. The tertiary benzylic trifluoroacetate Ph(CH3)C(CONMe2)(OCOCF3), 12, solvolyzes to give exclusively an elimination product. The β-CD3 isotope effect on rate was 1.15. There is, however, a larger isotope effect (2.5) in formation of the elimination product when Ph(CH2D)C(CONMe2)(OCOCF3) solvolyzes. The mechanism therefore has a minimum of two steps since the product-determining step and the rate-determining step have differing isotope effects. A concerted elimination mechanism is ruled out. The ortho-dimethyl-substituted cumyl trifluoroacetate 13 also solvolyzes to give an elimination product. The β-D6 isotope effect of 1.61 is in the "normal" range for a secondary isotope effect in a carbocation-forming reaction. This argues against a concerted elimination mechanism. These results contrast with the recent suggestion that cumyl systems give elimination product via a concerted elimination mechanism. The analogous tertiary benzylic systems 11-13 all give solvolytic elimination products via discrete cationic intermediates.

A NEW PALLADIUM-CATALYZED SYNTHESIS OF 1,2,3,4,4a,8b-HEXAHYDRO-1,4-METHANOBIPHENYLENES AND 2-PHENYLBICYCLOHEPT-2-ENES

Aromatic bromides react with bicyclohept-2-ene in the presence of palladium(0) coplexes and alkali phenoxides to give hexahydromethanobiphenylenes and phenylbicycloheptenes, probably via palladacyclic intermediates.Use of hindered phenoxides leads to selective cyclobutene ring closure.