Cyclooctadecanonaene or [18]annulene is an annulene
Annulenes are completely conjugated monocyclic hydrocarbons. They have the general formula CnHn or CnHn+1...

 with chemical formula . This hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....

 obeys Hückel's rule
Hückel's rule
In organic chemistry, Hückel's rule estimates whether a planar ring molecule will have aromatic properties. The quantum mechanical basis for its formulation was first worked out by physical chemist Erich Hückel in 1931...

 and is, therefore, an aromatic compound. The compound was first synthesised by Franz Sondheimer
Franz Sondheimer
-Early life:Sondheimer was born in Stuttgart, Germany in 1926 and, following the rise of the Nazis, fled to the United Kingdom in 1937.-Education:He was a pupil at Highgate School and subsequently studied chemistry, receiving his degree from Imperial College London.-Career:From 1949 to 1952,...



The original synthesis started by the Eglinton reaction of the di-alkyne
Alkynes are hydrocarbons that have a triple bond between two carbon atoms, with the formula CnH2n-2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature...

 1,5-hexadiyne with copper(II) acetate
Copper(II) acetate
Copper acetate, also referred to as cupric acetate, is the chemical compound with the formula Cu2 where OAc- is acetate . The hydrated derivative, which contains one molecule of water for each Cu atom, is available commercially. Anhydrous Cu2 is a dark green crystalline solid, whereas Cu22 is...

 in pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one C-H group replaced by a nitrogen atom...

 to give the trimer, followed by deprotonation
Deprotonation is the removal of a proton from a molecule, forming the conjugate base.The relative ability of a molecule to give up a proton is measured by its pKa value. A low pKa value indicates that the compound is acidic and will easily give up its proton to a base...

 and isomerization with potassium
Potassium is the chemical element with the symbol K and atomic number 19. Elemental potassium is a soft silvery-white alkali metal that oxidizes rapidly in air and is very reactive with water, generating sufficient heat to ignite the hydrogen emitted in the reaction.Potassium and sodium are...

Butanol or butyl alcohol can refer to any of the four isomeric alcohols of formula C4H9OH:*n-Butanol, butan-1-ol, 1-butanol, n-butyl alcohol;*Isobutanol, 2-methylpropan-1-ol, isobutyl alcohol;...

 in tert-butanol
tert-Butanol, or 2-methyl-2-propanol, is the simplest tertiary alcohol. It is one of the four isomers of butanol. tert-Butanol is a clear liquid with a camphor-like odor. It is very soluble in water and miscible with ethanol and diethyl ether...

 and was concluded with hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

 organic reduction with the Lindlar catalyst
Lindlar catalyst
A Lindlar catalyst is a heterogeneous catalyst that consists of palladium deposited on calcium carbonate and treated with various forms of lead. The lead additive serves to deactivate the palladium sites. A variety of "catalyst poisons" have been used including lead acetate and lead oxide. The...

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