39520-10-0

Basic information

• Product Name: Benzene, 1,1'-(2-ethenyl-2-methylcyclopropylidene)bis-
• CAS NO: 39520-10-0
• Molecular Formula: C18H18
• Molecular Weight: 234.341
• Mol File: 39520-10-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-(2-ethenyl-2-methylcyclopropylidene)bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-(2-ethenyl-2-methylcyclopropylidene)bis-(39520-10-0)
• EPA Substance Registry System: Benzene, 1,1'-(2-ethenyl-2-methylcyclopropylidene)bis-(39520-10-0)

Safety Data

• Hazardous Substances Data: 39520-10-0(Hazardous Substances Data)

Upstream product

• 908093-98-1 diazodiphenylmethane 
• 78-79-5 isoprene 
• 3129-17-7 diphenylcarbene 
• 67-56-1 methanol 
• 470-35-9 tetraphenyloxirane 

Downstream Products

• 57393-10-9 3-(Benzhydrylidene-amino)-4-isopropenyl-cyclopent-2-ene-1,1,2-tricarbonitrile 

Relevant articles and documents

Diazodiphenylmethane and monosubstituted butadienes: Kinetics and a new chapter of vinylcyclopropane chemistry

Diazodiphenylmethane (DDM) undergoes cycloadditions to 1-substituted buta-1,3-dienes exclusively at the C(3)=C(4) bond. At room temperature, the N2 loss from the initially formed 4,5-dihydro-3H-pyrazoles 2 is faster than the cycloaddition and furnishes the vinylcyclopropane derivatives 7 and 9 with structural retention at the C(1)=C(2) bond. 2-Substituted butadienes react with DDM at the C(3)=C(4) bond to give 12; isoprene, however, affords 3,4/1,2 products in the ratio of 86:14. DDM is a nucleophilic 1,3-dipole: 1-Cyanobutadiene reacts 400 times faster than 1-methoxybuta-1,3-diene (DMF, 40°). The log k2 for the additions to six 1-substituted butadienes show a linear correlation with σp (Hammett) and ρ = +2.9; the log k2 of five 2-substituted butadienes are linearly related to Taft's σI (ρ = +1.7). The structures of the vinylcyclopropanes 7, 9, and 12 are established by NMR spectra and oxidation. A cyclopropyl carbinyl cation is made responsible for the isomerization of 12, R = Ph, Me, by acetic acid to 4-substituted 1,1-diphenylpenta-1,3-dienes 25 and 29; TsOH at 200° converts 25 further to 9,10-dihydro-9-methyl-10-phenyl-9,10-ethanoanthracene (27). Thermal rearrangement of 7, 9, and 12 at 200-300° produces the 3- or 1-substituted 4,4-diphenylcyclopentenes 30 and 31. These give the same mass spectra as the vinylcyclopropanes, and an open-chain distonic radical cation is suggested as common intermediate. Besides spectroscopic evidence for the cyclopentene structures, hydrogenation and epoxidation are described; NMR data support the trans-attack by perbenzoic acid.

TEMPERATURE DEPENDENCE OF THE REACTIONS OF SINGLET AND TRIPLET DIPHENYLCARBENE. EVIDENCE FOR REVERSIBLE YLIDE FORMATION IN THE REACTION WITH ALCOHOLS

The temperature dependences of the reaction of singlet diphenylcarbene are consistent with reversible intermediate formation.

LASER FLASH SPECTROMETRIC INVESTIGATIONS OF BIRADICALS AND CAGED RADICAL PAIRS

The use of laser flash spectroscopic techniques allows the detection, identification and dynamic analysis of biradicals and caged radical pairs in fluid solution at ambient temperatures.The conventional flash spectroscopic device has been advanced with the advent of the Excimer Laser, as an excitation source of the optical multichannel analyzer (OMA) as a detector system and of the transient digitizer (TD) as a data collector and analyzer.The Excimer Laser, in addition to serving as an excitation source, may also induce novel photophysical and/or photochemical events as a result of the unusually high intensities produced by such devices.Examples are given of the use of Excimer Laser-OMA and Excimer Laser-TD systems to study the dynamics of radical pairs that are caged in micelle aggregates and to study novel emissions produced by photoexcitation of benzophenone and substituted benzophenones.