Aryne

in chemistry, an aryne is an uncharged reactive intermediate derived from an aromatic system by removal of two ortho substituents, leaving two orbitals with two electrons distributed between them. In analogy with carbenes and nitrenes, an aryne has a singlet state and a triplet state. The name benzyne (1) for the simplest aryne is open for critisism because it implies an alkyne bond which is not the case, a better name is dehydrobenzene. Benzyne is stabilized by resonance between structures 1 and 2 and a more accurate depiction is 3. A suitable chemical trap for benzyne is a cyclobutadiene.

references

• Gilchrist T.C.;Rees C.W.; (1969) carbenes, nitrenes and arynes. Nelson. London