24578-28-7

Basic information

• Product Name: p-(2-Isopropylidenecyclopropyl)toluene
• Synonyms: p-(2-Isopropylidenecyclopropyl)toluene
• CAS NO: 24578-28-7
• Molecular Formula: C₁₃H₁₆
• Molecular Weight: 172.27
• Mol File: 24578-28-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 239.9±20.0 °C(Predicted)
• Appearance: /
• Density: 0.981±0.06 g/cm3(Predicted)
• CAS DataBase Reference: p-(2-Isopropylidenecyclopropyl)toluene(CAS DataBase Reference)
• NIST Chemistry Reference: p-(2-Isopropylidenecyclopropyl)toluene(24578-28-7)
• EPA Substance Registry System: p-(2-Isopropylidenecyclopropyl)toluene(24578-28-7)

Safety Data

• Hazardous Substances Data: 24578-28-7(Hazardous Substances Data)

Upstream product

• 598-25-4 Dimethylallene 
• 104-82-5 4-Methylbenzyl chloride 
• 104-87-0 4-methyl-benzaldehyde 
• 40739-81-9 p-tolualdehyde p-toluenesulfonylhydrazone 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 66680-86-2 isobutenyltributyltin 
• 65108-26-1 2-p-Tolyl-3,3-dimethylmethylenecyclopropane 
• 24519-03-7 5,5-dimethyl-N-nitroso-2-oxazolidone 

Relevant articles and documents

Cobalt- and Silver-Promoted Methylenecyclopropane Rearrangements

The rate of the methylenecyclopropane rearrangement is enhanced by an alkyne-Co2(CO)6 complex bonded to the para position of a benzene ring. This is explained by a stabilizing effect on the transition state leading to the biradical intermediate. Computational studies indicate that the benzylic-type biradical intermediate is stabilized by a delocalization mechanism, where spin is delocalized onto the two cobalt atoms. Silver cation also enhances the rate of the methylenecyclopropane rearrangement. Computational studies suggest that silver cation can also stabilize a benzylic radical by spin delocalization involving silver. In the case of the silver-promoted reactions, the rate enhancements in a series of aryl-substituted methylenecyclopropanes correlate with σ+ values. The question remains open as to whether the silver-catalyzed methylenecyclopropane rearrangement proceeds via an argento-stabilized biradical or whether the reaction involves an argento-substituted allylic cation.

Nature of Alkylidenecarbenes Generated from Alkenyl(phenyl)iodonium Tetrafluoroborates via Base-Induced α-Elimination

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Rearrangement of 2-Aryl-3,3-dimethylmethylenecyclopropanes. Substituent Effects on a Nonpolar Radical-Like Transition State

The effect of substituents on the thermal rearrangement of 2-aryl-3,3-dimethylmethylenecyclopropanes, 4, to 2-arylisopropylidenecyclopropanes, 5, has been determined.This has allowed an evaluation of substituent effects on a free-radical-like transition state devoid of polar character.In general, no correlation of all the data could be obtained with Hammett ? values.Electronegative meta substituents slightly decreased rates (ρ = -0.16).Conjugating substituents such as CN and CO2CH3 in the para position increased rates.The effect of the p-CF3 group was rate enhancing.The potential for C-F hyperconjugative stabilization is discussed as a radical-stabilizing feature.Thiomethyl and trimethylsilyl substituents in the para position increased rates.The possibility of radical-stabilizing interactions with vicinal ?* and ? orbitals is discussed. p-Methoxy substitution increased rates while p-fluoro substitution slowed rates.Resonance delocalization involving charge-separated forms 10a and 11 was suggested to be less favorable in the case of p-fluoro substitution.Delocalization involving an expanded octet accounted for increased rearrangement rates of p-Cl and p-Br-substituted 4.