A new class of aminocyclitol derivatives with the bicyclo[4.2.0]octane skeleton was synthesized starting from cyclooctatetraene. Photooxygenation of trans-7,8-diacetoxy- and cis-7,8-dichlorobicyclo[4.2.0]octa-2,4-diene afforded the bicyclic endoperoxides. Reduction of the latter with thiourea followed by a Pd(0) catalyzed ionization/cyclization reaction gave the corresponding oxazolidinone deri...

Pirfenidone, an oral anti-fibrotic and anti-inflammatory medication used for the treatment of idiopathic pulmonary fibrosis (IPF), has been proposed to treat post-COVID pneumonia (PF). However, pirfenidone displays side effects which include hepatotoxicity anorexia. Cubane cyclooctatetraene (COT) derivatives were prepared as bioisostere/biomotif replacements phenyl ring explore potential change...

A series of free base meso-tetraarylporphyrins functionalized with substituents containing one, two, and four cyclooctatetraene (COT) moieties have been obtained characterized by spectral photophysical studies. Three COT-free porphyrins served as reference compounds. COT is a triplet quencher, well-known to enhance the photostability several, but not all, fluorophores. In case porphyrins, subst...

We consider a set of nine polycyclic conjugated hydrocarbons, which includes at one extreme benzene, the prototype of aromatic compounds, and at the other extreme cyclooctatetraene, a well-known nonaromatic compound, while the remaining seven compounds illustrate molecules of decreasing degree of aromaticity. Using the model of conjugated circuits for calculations of ring currents, we report on...

Cyclooctatetraene (COT), the first 4nπ-electron system to be studied, adopts an inherently nonplanar tub-shaped geometry of D2d symmetry with alternating single and double bonds, and hence behaves as a nonaromatic polyene rather than an antiaromatic compound. Recently, however, considerable 8π-antiaromatic paratropicity has been shown to be generated in planar COT rings even with the bond alter...

The planarity and 10 π-electron aromaticity of the free cyclooctatetraene dianion (C8H8 2−, COT2−) have been questioned recently on the basis of conflicting density functional and second-order Møller−Plesset perturbation computations. Rigorous coupled-cluster methods are employed here to establish the structure and properties of COT2−. Like many multiply charged anions, COT2− exists in isolatio...