82323-32-8

Basic information

• Product Name: 2-methylene-4-methyl-5,6-diphenyltetracyclo<5.4.0.0^1,5.0^4,6>undeca-8,10-diene
• Synonyms: 2-methylene-4-methyl-5,6-diphenyltetracyclo<5.4.0.0^1,5.0^4,6>undeca-8,10-diene
• CAS NO: 82323-32-8
• Molecular Weight: 322.45
• Mol File: 82323-32-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-methylene-4-methyl-5,6-diphenyltetracyclo<5.4.0.0^1,5.0^4,6>undeca-8,10-diene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylene-4-methyl-5,6-diphenyltetracyclo<5.4.0.0^1,5.0^4,6>undeca-8,10-diene(82323-32-8)
• EPA Substance Registry System: 2-methylene-4-methyl-5,6-diphenyltetracyclo<5.4.0.0^1,5.0^4,6>undeca-8,10-diene(82323-32-8)

Safety Data

• Hazardous Substances Data: 82323-32-8(Hazardous Substances Data)

Upstream product

• 67300-99-6 1-phenylethenylmagnesium bromide 
• 6006-81-1 3-hydroxy-2-phenylpropene 
• 3360-52-9 3-chloro-2-phenylprop-1-ene 
• 82323-13-5 3-methyl-1,2-diphenyl-3-(2-phenylallyl)cyclopropene 

Downstream Products

• 82323-29-3 2-methyl-1,4,6-triphenyltricyclo<2.2.0.0^2,6>hexane 
• 2781-85-3 cyclopropene 
• 82323-13-5 3-methyl-1,2-diphenyl-3-(2-phenylallyl)cyclopropene 

Relevant articles and documents

Cyclopropene Photochemistry. Mechanistic and Exploratory Organic Photochemistry

Four new cyclopropenes have been synthesized and their photochemistry has been investigated.Thus, 3-methyl-1,2-diphenyl-3-(2-phenylallyl)cyclopropene was found on direct photolysis to afford four photoproducts, the two major products of which derived from novel photochemistry. 2-Methylene-4-methyl-5,6-diphenyltetracyclo1,504,6>undeca-8,10-diene derived from cycloaddition of the excited cyclopropenyl ? bond to the C-1,C-2 ? bond of the phenyl of the 2-phenylallyl side chain.The quantum yield for this novel transformation was 0.023.A second photoproduct was 2-methyl-1,4,6-triphenyltricyclo2,6>hexane.This product results from a formal cycloaddition of the excited cyclopropenyl ? bond to the allyl double bond.A diradical mechanism is structurally equivalent.Formation of such a tricyclic 2,6> system is normally not found in direct irradiations.The quantum yield for this product was 0.088.Also formed was 3-methyl-1,2,5-triphenylbicyclohex-2-ene with an efficiency of 0.019.This product is understood as deriving either (i) from cyclopropene opening to a carbene which then adds to the allyl ? bond or (ii) from a bicyclic diradical arising from vinyl-vinyl bonding.The fourth photoproduct is 2-methyl-1,3-diphenyl-3-(2-phenylallyl)cyclopropene.The efficiency was 0.018.The bicyclic diradical above provides a common species leading to the last three products.Sensitization led only to the first two products: the tetracyclic diene (φ=0.26) and the tricyclo2,6>hexane (φ=0.15).Product structures were established by X-ray, degradation, independent synthesis, and spectral analysis.In addition, the photochemistry of cis- and trans-2,6-dimethyl-1,6-diphenylspirooct-1-ene was investigated.Stereoisomerization resulted from the singlet but not the triplet.Mechanisms for the above transformations are considered.Finally, corresponding thermal chemistry exhibited by the above compounds was investigated.