57273-96-8

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 2216-94-6 phenylpropynoic acid ethyl ester 

Downstream Products

• 357670-29-2 3-phenylbicyclo[2.2.1]hepta-2,5-diene-2-methanol 
• 950-91-4 3-phenyl-2,5-norbornadiene-2-carboxylic acid 
• 357670-32-7 2-[2-(3-phenylbicyclo[2.2.1]hepta-2,5-dien-2-ylmethoxy)ethoxy]tetrahydro-2H-pyran 
• 357670-37-2 2-(3-phenylbicyclo[2.2.1]hepta-2,5-dien-2-ylmethoxy)ethanol 

Relevant academic research and scientific papers

Photoswitchable Norbornadiene–Quadricyclane Interconversion Mediated by Covalently Linked C60

The synthesis and properties of various norbornadiene/quadricyclane (NBD/QC) fullerene hybrids are reported. By cyclopropanation of C60 with malonates carrying the NBD scaffold a small library of NBD–fullerene monoadducts and NBD–fullerene hexa

Solar Energy Storage: Competition between Delocalized Charge Transfer and Localized Excited States in the Norbornadiene to Quadricyclane Photoisomerization

We describe for the first time the full reaction coordinate regarding the photoisomerization of red-absorbing norbornadienes (NBDs) to quadricyclanes (QCs). Our studies go beyond steady-state investigations by using an arsenal of time-resolved techniques. Importantly, the red absorption of NBDs is made possible by a different charge-transfer character; adjusting its strength enables control over the photoreversibility of the rearrangement. In the case of strong charge-transfer character (a weakly electron-withdrawing ester and a strongly electron-donating dimethylaniline), photoirradiation with visible light into the delocalized charge-transfer absorption of NBD affords QC reversibly. In stark contrast, UV photoirradiation into the NBD localized excited state leads to a photoinduced degradation and cannot be back-isomerized to NBD under any circumstances. If the charge-transfer character is weak (a weakly electron-withdrawing ester and a weakly electron-donating phenyl), reversibility is seen independently of the photoirradiation light.

Intramolecular 1,3-dipolar cycloadditions of norbornadiene-tethered nitrones

Efficient routes to the synthesis of norbornadiene-tethered nitrones have been developed, and their intramolecular 1,3-dipolar cycloadditions were studied. The cycloadditions occurred in moderate to good yields for a variety of substrates and were found to be highly regio- and stereoselective, giving single regio- and stereoisomers in most cases.