Cyclobutadiene and Relatives

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Cyclobutadiene: the antiaromatic paradigm?

There is probably no other single molecule that has fascinated experimental and theoretical chemists so consistently over the past 40 years as has cyclobutadiene (CBD). On average, 16 publications which deal, in one form or another, with the parent compound C4H4 and 40 which deal with cyclobutdienes in general have appeared in every year of this time span, and there are probably many more on de...

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Cyclobutadiene and Its Metal Complexes

The practical and theoretical problems associated with the cyclobutadiene molecule have concerned organic chemists for over one hundred years and, as is well known, this compound has played a particularly interesting role in the development of organic chemistry. The importance of the system to organic chemists stems mainly from the fact that the molecule is a cyclic conjugated system for which,...

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Intramolecular cycloadditions of cyclobutadiene with olefins.

Intramolecular cycloadditions between cyclobutadiene and olefins can provide highly functionalized cyclobutene-containing products. The outcome of the reaction depends on the nature of the tether connecting the two reactive partners in the cycloaddition. Electronically unactivated olefins attached to cyclobutadiene through a three-atom, heteroatom-containing tether yield successfully the desire...

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Is cyclobutadiene really highly destabilized by antiaromaticity?

The high energy of cyclobutadiene (CBD) is not due primarily to "anti-aromaticity," but rather to angle strain, torsional strain, and Pauli repulsion between the parallel CC bonds. Estimations including block-localized wavefunction (BLW) computations conclude that the enormous ring strain (ca. 60 kcal mol(-1)) far exceeds its antiaromatic destabilization (only 16.5 kcal mol(-1)).

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Polymerization of thiophene containing cyclobutadiene Co cyclopentadiene complexes

To understand the charge transport ability of the metal coordinated cyclobutadiene, a series of cyclobutadiene cobalt cyclopentadiene (CbCoCp) omplexes containing electrochemically polymerizable thiophene units were synthesized. The complexes were electrochemically polymerized nd the resulting polymers were characterized by cyclic voltammetry, in situ conductivity and UV–vis spectroelectrochemi...

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ژورنال

عنوان ژورنال: Nature

سال: 1967

ISSN: 0028-0836,1476-4687

DOI: 10.1038/216619b0