59183-40-3

Basic information

• Product Name: Benzene, 1,1'-(3,3-dimethyl-1,2-cyclopropanediyl)bis-, trans-
• CAS NO: 59183-40-3
• Molecular Formula: C17H18
• Molecular Weight: 222.33
• Mol File: 59183-40-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-(3,3-dimethyl-1,2-cyclopropanediyl)bis-, trans-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-(3,3-dimethyl-1,2-cyclopropanediyl)bis-, trans-(59183-40-3)
• EPA Substance Registry System: Benzene, 1,1'-(3,3-dimethyl-1,2-cyclopropanediyl)bis-, trans-(59183-40-3)

Safety Data

• Hazardous Substances Data: 59183-40-3(Hazardous Substances Data)

Upstream product

• 56763-59-8 (E)-(3-methylbut-1-ene-1,3-diyl)dibenzene 
• 100-52-7 benzaldehyde 
• 67437-47-2 cis-1,2-diphenyl-3,3-dimethylcyclopropane 
• 50555-61-8 3,3-dimethyl-1,2-diphenyl-1-cyclopropene 
• 201230-82-2 carbon monoxide 
• 67437-45-0 3-methyl-1,3-diphenylbutan-1-ol 
• 917-54-4 methyllithium 
• 33044-88-1 (3,3-dibromocyclopropane-1,2-diyl)dibenzene 
• 74-88-4 methyl iodide 

Relevant articles and documents

The di-π-methane reaction of 3,3-dimethyl-1,3-diphenylpropene revisited: Dynamics and barriers for competitive singlet state reactions [7]

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Temperature-dependent photochemistry of 1,3-diphenylpropenes. The di-π-methane reaction revisited

The temperature-dependent photochemical behavior of 1,3-diphenylpropene and several of its 3-substituted derivatives has been investigated over a wide temperature range. The singlet state is found to decay via two unactivated processes, fluorescence and intersystem crossing, and two activated processes, trans,-cis isomerization and phenyl-vinyl bridging. The latter activated process yields a diradical intermediate which partitions between ground-state reactant and formation of the di-π-methane rearrangement product. Kinetic modeling of temperature-dependent singlet decay times and quantum yields of fluorescence, isomerization, di-π-methane rearrangement, and nonradiative decay provides rate constants and activation parameters for each of the primary and secondary processes. Substituents at the 3-position are found to have little effect on the electronic spectra or unactivated fluorescence and intersystem crossing pathways. However, they do effect the activated primary and secondary processes. Thus, the product ratios are highly temperature dependent.

The Preparation and Photolysis of (E)-1-Aryl-3-methyl-3-phenylbut-1-enes

Reaction of 2-methyl-2-phenylpropylmagnesium chloride with benzaldehyde in tetrahydrofuran gave, 2,7-dimethyl-2,4,5,7-tetraphenyloctane-4,5-diol as a 1:2 mixture of clear transparent crystalline plates (meso) and needles (+/-), 3-methyl-1,3-diphenylbutan-1-one, benzyl alcohol, 2-methyl-2-phenyl-propane and a low yield of 3-methyl-1,3-diphenylbutan-1-ol.The distinction between the meso- and the (+/-)-diols was unequivocal because the unique space group of the former requires the dimeric molecules to lie about a crystallographic centre of symmetry.The mechanism involved in the formation of the products of the Grignard reaction is examined.By careful choice of reaction conditions a series of 1-aryl-3-methyl-3-phenylbutan-1-ols were prepared.Dehydration of the 1-aryl-3-methyl-3-phenylbutan-1-ols with p-toluenesulfonic acid and a short reaction time gives (E)-1-aryl-3-methyl-3-phenylbut-1-enes but longer reaction times afford 3-aryl-1,1-dimethylindanes.Photolysis of the (E)-1-aryl-3-methyl-3-phenylbut-1-enes affords (Z)-1-aryl-3-methyl-3-phenylbut-1-enes and trans-1-aryl- 3,3-dimethyl-2-phenylcyclopropanes.Extended photolysis gives 4-aryl-2-methyl-3-phenylbut-1-enes via trans-1-aryl-3,3-dimethyl-2-phenylcyclopropane by rupture of the cyclopropyl bond adjacent to the aryl substituent.