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Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C 14 H 10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation. [13]
There is no more than 1 sigma bond between any two atoms. Molecules with rings have additional sigma bonds, such as benzene rings, which have 6 C−C sigma bonds within the ring for 6 carbon atoms. The anthracene molecule, C 14 H 10, has three rings so that the rule gives the number of sigma bonds as 24 + 3 − 1 = 26. In this case there are 16 ...
The anthracene molecule allows three resonance structures, each with a circle in one ring and two sets of double bonds in the other two. Following rule 4 above, anthracene is better described by a superposition of these three equivalent structures, and an arrow is drawn to indicate the presence of a migrating π-sextet.
9,10-Dihydroanthracene is an organic compound that is derived from the polycyclic aromatic hydrocarbon anthracene. Several isomers of dihydroanthracene are known, but the 9,10 derivative is most common. It is a colourless solid that is used as a carrier of H 2 as a hydrogen-donor. [2]
Sigmatropic rearrangements are concisely described by an order term [i,j], which is defined as the migration of a σ-bond adjacent to one or more π systems to a new position (i−1) and (j−1) atoms removed from the original location of the σ-bond. [3]
Transition metal alkane complexes (e.g., a methane complex) that bind solely through the C–H bond are also known but structurally characterized examples are rare, as C–H σ-bonds are generally poor electron donors, and, in many cases, the weakened C–H bond cleaves completely (C–H oxidative addition) to form a complex of type M(R)(H). [1]
Sigma bond cleavage is most commonly observed in molecules that can produce stable cations, such as saturated alkanes or secondary and tertiary carbocations. This occurs when an alpha electron is removed. The C-C bond elongates and weakens causing fragmentation. Fragmentation at this site produces a charged and a radical fragment. [2]
[4+4] photocycloaddition approaches to the creation of cyclooctanoid systems offer several appealing features, including convergent assembly of the eight-membered ring from two relatively simpler four-carbon fragments, formation of two new carbon-carbon bonds, and the potential for introduction of up to four new stereocenters in one step.