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  2. Cyclobutadiene - Wikipedia

    en.wikipedia.org/wiki/Cyclobutadiene

    Cyclobutadiene is an organic compound with the formula C 4 H 4. It is very reactive owing to its tendency to dimerize . Although the parent compound has not been isolated, some substituted derivatives are robust and a single molecule of cyclobutadiene is quite stable.

  3. Ladderane - Wikipedia

    en.wikipedia.org/wiki/Ladderane

    The first step in forming the syn product involves the generation of 1,3-cyclobutadiene by treatment of cis-3,4-dichlorocyclobutene with sodium amalgam. The reactant passes through a metalated intermediate before forming 1,3-cyclobutadiene, which can then dimerize to form the syn-diene.

  4. Aromaticity - Wikipedia

    en.wikipedia.org/wiki/Aromaticity

    Two different resonance forms of benzene (top) combine to produce an average structure (bottom). In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected by the stabilization of conjugation alone.

  5. Butadiene - Wikipedia

    en.wikipedia.org/wiki/Butadiene

    1,3-Butadiene (/ ˌ b juː t ə ˈ d aɪ iː n / ⓘ) [8] is the organic compound with the formula CH 2 =CH-CH=CH 2. It is a colorless gas that is easily condensed to a liquid. It is a colorless gas that is easily condensed to a liquid.

  6. Homoaromaticity - Wikipedia

    en.wikipedia.org/wiki/Homoaromaticity

    Homoaromaticity, in organic chemistry, refers to a special case of aromaticity in which conjugation is interrupted by a single sp 3 hybridized carbon atom. Although this sp 3 center disrupts the continuous overlap of p-orbitals, traditionally thought to be a requirement for aromaticity, considerable thermodynamic stability and many of the spectroscopic, magnetic, and chemical properties ...

  7. Clar's rule - Wikipedia

    en.wikipedia.org/wiki/Clar's_rule

    Clar's rule states that for a benzenoid polycyclic aromatic hydrocarbon (i.e. one with only hexagonal rings), the resonance structure with the largest number of disjoint aromatic π-sextets is the most important to characterize its chemical and physical properties. Such a resonance structure is called a Clar structure. In other words, a ...

  8. Annulene - Wikipedia

    en.wikipedia.org/wiki/Annulene

    Using this form of nomenclature 1,3,5,7-cyclooctatetraene is [8]annulene and benzene is [6]annulene (and occasionally referred to as just 'annulene'). [ 2 ] [ 3 ] The discovery that [18]annulene possesses a number of key properties associated with other aromatic molecules was an important development in the understanding of aromaticity as a ...

  9. Bicyclobutane - Wikipedia

    en.wikipedia.org/wiki/Bicyclobutane

    Bicyclo[1.1.0]butane is an organic compound with the formula C 4 H 6. It is a bicyclic molecule consisting of two cis -fused cyclopropane rings, and is a colorless and easily condensed gas. [ 1 ] Bicyclobutane is noted for being one of the most strained compounds that is isolatable on a large scale — its strain energy is estimated at 63.9 ...