Reatividade de ciclopropenonas frente a nucleófilos e sua correlação com potenciais de redução em meio aprótico

Poly(cyclopropenone)s: Formal Inclusion of the Smallest Hückel Aromatic into π-Conjugated Polymers

“…Outside of Zefirov’s recent work, there are very few examples of heteroaromatic rings appended to cyclopropenone/cyclopropenium rings relative to the vast library of phenyl-substituted molecules. Furthermore, very little work has studied the oxidative electrochemistry of cyclopropenones to provide useful insights for electropolymerization strategies . Therefore, we set out to expand the functional scope of the cyclopropenone core through the preparation of a variety of thiophene derivatives.…”

Structural and reactivity analyses of 2-benzylamino-1,4-naphthoquinone by X-ray characterization, electrochemical measurements, and dft single-molecule calculations

“…25 Thus, to understand the electronic behavior of naphthoquinone 1, some theoretical and experimental parameters were investigated. In this way, the calculated HOMO-LUMO for conformers 1a and 1b are shown in Figure 3.…”

Heterocycles from cyclopropenones

“…Previously, Cunha and Rocha had reported that 1,6-diisopropyl-2,7-diphenyl-4-oxaspiro-[2.4]hepta-1,6-dien-5-one ( 55 ) was synthesized in 48% yield, via refluxing 2-isopropyl-3-phenyl-cycloprop-2-en-1-one ( 1z ) in dioxane in the presence of copper chloride (CuCl) for 12 h, as shown in Scheme 36. 86…”

“…On reacting 2-isopropyl-3-phenylcycloprop-2-en-1-one ( 1z ) with 1-phenyl-2-(triphenyl-phosphoranylidene)ethanone ( 86 ) in benzene for 5 h, 4-isopropyl-3,6-diphenyl-2 H -pyran-2-one ( 87a ) was obtained in 35% yield (Scheme 53). 86…”

“…2-Benzyl-3-isopropylquinoxaline ( 140 ) was synthesized via reacting 2-isopropyl-3-phenylcycloprop-2-en-1-one ( 1z ) with benzene-1,2-diamine ( 139 ) in diethyl ether for 8 h and in the presence of 1 H -pyrazole as a catalyst (Scheme 86). 86…”