72610-87-8

Basic information

• Product Name: Bicyclo[4.2.0]octa-1,3,5-triene, 7-bicyclo[4.2.0]octa-1,3,5-trien-7-ylidene-, (7E)-
• CAS NO: 72610-87-8
• Molecular Formula: C16H12
• Molecular Weight: 204.271
• Mol File: 72610-87-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Bicyclo[4.2.0]octa-1,3,5-triene, 7-bicyclo[4.2.0]octa-1,3,5-trien-7-ylidene-, (7E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[4.2.0]octa-1,3,5-triene, 7-bicyclo[4.2.0]octa-1,3,5-trien-7-ylidene-, (7E)-(72610-87-8)
• EPA Substance Registry System: Bicyclo[4.2.0]octa-1,3,5-triene, 7-bicyclo[4.2.0]octa-1,3,5-trien-7-ylidene-, (7E)-(72610-87-8)

Safety Data

• Hazardous Substances Data: 72610-87-8(Hazardous Substances Data)

Upstream product

• 3469-06-5 benzocyclobutenone 
• 78329-07-4 Bicyclo[4.2.0]octa-1,3,5-trien-7-yl-triphenyl-phosphonium; bromide 
• 69139-15-7 Sodium Salt of Benzocyclobutenone Tosylhydrazone 
• 72610-89-0 Lithium Salt of Benzocyclobutenone Tosylhydrazone 

Downstream Products

• 87-41-2 2-benzofuran-1(3H)-one 
• 3469-06-5 benzocyclobutenone 
• 40261-88-9 dibenzocycloocten-11,12(5H,6H)-dione 
• 113446-65-4 spiro-1'(3'H)-one 

Relevant articles and documents

Synthesis, structural characterization and photoisomerization of cyclic stilbenes

Six cyclic stilbene derivatives with hindered free rotation around the C(vinyl)-C(phenyl) single bond were synthesized by McMurry coupling. The torsion angles around the double and the single bond, and the CC bond length were obtained for many of the compounds from their solid-state structures. The photochemical isomerization was subsequently investigated for all derivatives under various conditions. The parent 1-(1-tetralinylidene)tetralin underwent efficient oxidative electrocyclization. The 2,2,2′,2′- tetramethylated analogue was resistant towards photooxidation, however, its cis-isomer thermally reisomerized to the more stable trans-isomer.

Cyclic trans-stilbenes: Synthesis, structural and spectroscopic characterization, photophysical and photochemical properties

trans-Stilbene and several cyclic derivatives with hindered free rotation around the C(vinyl)-C(phenyl) single bond were studied by various spectroscopic techniques. Those derivatives which contain 6- or 7-membered aliphatic rings do not exhibit any measurable S1 → S0 fluorescence. The introduction of two methoxy groups into the 6-membered aliphatic ring derivative accelerates its photoreactivity to such an extent that fluorescence or resonance Raman spectroscopy investigations become impossible. The introduction of aliphatic rings has only a little effect on the frequency of the phenyl-ring stretching vibrations, but pronounced ones on the IR and Raman intensities. The frequency of the vinylic stretching mode is downshifted between 5 and 100 cm-1 except in the case of the derivative with the 4-membered ring, which experiences a hypsochromic shift of 80 cm-1. Only trans-stilbene and its 4-membered cyclic analogues were amenable to fluorescence lifetime measurements. Analysis of VT-NMR spectra of stilbene 7 reveals a barrier of 15.9 kcal mol-1 for equilibration of aliphatic equatorial and axial H-atoms.

Radical-Stabilization-Energy - the MMEVBH Force Field

Making use of the VB method of Malrieu et al. a force field has been developed, which allows to calculate heats of formation of hydrocarbons (conjugated and non-conjugated olefins, radicals and diradicals) with high accuracy.With this method radical stabilization energies (RSE) for a great number of delocalized radicals are calculated and compared with experimental values, derived from shock-tube measurements of dissociation energies or from rotational barriers of substituted olefins.A detailed analysis of the RSE with respect to structure, substituents, strain, and aromaticity is presented. - Key Words: Resonance energy / Heats of formation / Single pulse shock tube / Intrisic rotational barrier