5164-35-2

Usage

Safety Profile

This strained ring compound mayexplode spontaneously. When heated to decomposition itemits acrid smoke and fumes.

InChI:InChI=1/C5H6/c1-2-5-3-4(1)5/h1-2,4-5H,3H2

Upstream product

• 542-92-7 cyclopenta-1,3-diene 

Downstream Products

• 82106-91-0 (1R,2R,4S,5R)-8-Phenyl-6-oxa-7-aza-tricyclo[3.3.0.0^2,4]oct-7-ene 
• 15971-63-8 4-phenyl-2,4,6-triazatricyclo[3.2.1.0(2,6)]dec-8-ene-3,5-dione 
• 61195-22-0 4-Methyl-2,4,6-triaza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 89406-15-5 (1S,2R,4S,5R)-8,8-Diphenyl-6,7-diaza-tricyclo[3.3.0.0^2,4]oct-6-ene 
• 89406-14-4 (1S,2R,4S,5R)-8-Phenyl-6,7,8-triaza-tricyclo[3.3.0.0^2,4]oct-6-ene 
• 542-92-7 cyclopenta-1,3-diene 
• 25073-23-8 (Z)-(4RS)-4,5-epoxypent-2-enal 

Relevant academic research and scientific papers

Photochemistry of cyclopentadiene isolated in low-temperature argon matrices

The photochemistry of cyclopentadiene isolated in low-temperature argon matrices was studied by means of IR and UV/VIS spectroscopy. Bicyclo[2.1.0]pent-2-ene was formed by the irradiation of matrix-isolated cyclopentadiene using a super-high-pressure mercury lamp. When the matrix-isolated cyclopentadiene was irradiated with shorter wavelength using a low-pressure mercury lamp, further reactions of bicyclo[2.1.0]pent-2-ene were found to produce allylacetylene and vinylallene. While the photochemistry of cyclopentadiene to form bicyclo[2.1.0]pent-2-ene is known in a solution system, the production of allylacetylene and vinylallene in a matrix-isolated system has never been previously reported. The assignments of the species and the determination of the reaction mechanisms were performed using molecular orbital calculations.

Heats of Hydrogenation, II. Heats of Hydrogenation of Bicyclopent-2-ene, an Antiaromatic System

The heat of hydrogenation of the olefinic double bond in bicyclopent-2-ene (2) and in the 5,5-dimethyl derivative 22 has been determined (42.5 and 42.0 kcal mol-1).By comparison with the heat of hydrogenation of the double bond in bicyclohex-2-ene (10) and bicyclohept-6-ene (9) an antiaromatic destabilisation of 10 kcal mol-1 is demonstrated.The antiaromaticity of 2 is also manifested in its high dienophilic reactivity.The rate of the reaction of 2 with 1,3-cyclopentadiene (6) is enhanced by a factor of 4.5 * 104 compared to the analogous reaction of bicyclooct-7-ene (8).