115395-24-9

Upstream product

• 100-02-7 4-nitro-phenol 
• 64858-88-4 8,9-Dicarboxy-10,11-dimethyl<5.2.2>propella-8,11-dien 
• 1785-53-1 undeca-2,9-diyne 
• 66016-85-1 8,9-Bis(methoxycarbonyl)-10,11-dimethyl<5.2.2>propella-8,11-dien 

Downstream Products

• 115395-28-3 10,11-Dimethyl-bicyclo[5.2.2]undeca-1⁽⁹⁾,7,10-triene-8,9-dicarboxylic acid bis-(4-nitro-phenyl) ester 

Relevant academic research and scientific papers

ZUR STABILISIERUNG VON PARACYCLOPHANEN DURCH SUBSTITUTION AM BENZOLRING

A relatively efficient route to substituted paracyclophanes 11 is described.Diels Alder reaction of the pentamethylenecyclobutadienes 3 and 4, prepared in situ, with acetylenes E-CC-E (5, E=electron withdrawing group) gives a mixture of Dewar benzenes, from which the 1,4-bridged isomer 7 is conveniently isolated after aromatization of the other isomers.Irradiation (254 nm) of 7 at 220 K establishes a photo equilibrium between 7 and 11 with 2-15 percent of the latter, depending on E.The aromatic character of 11 is derived from the UV- and 1H-NMR spectra; at 220K, two conformational isomers 11' and 11'' can be discerned.Although most 11 are thermally more stable than the parent compound paracyclophane, they slowly decompose in solution at room temperature.