Adamantane

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Adamantane

Adamantane (tricyclo[3.3.1.1^3,7]decane) is a colourless, crystalline compound with a camphor

Camphor

Camphor is a waxy, white or transparent solid with a strong, aromatic odor. It is a terpenoid with the chemical formula carbon10hydrogen16oxygen....
-like odour. With a formula C₁₀H₁₆, it is a cycloalkane

Cycloalkane

Cycloalkanes are types of alkanes which have one or more rings of carbon atoms in the chemical structure of their molecules. Alkanes are types of Organic compound hydrocarbon Chemical compound which have only single chemical bonds in their chemical structure....
and also the simplest diamondoid

Diamondoid

Petroleum

Petroleum or crude oil is a naturally occurring, flammable liquid found in rock formations in the Earth consisting of a complex mixture of hydrocarbons of various molecular weights, plus other organic compounds....
in 1933. Its name derived from the Greek adamantinos (relating to steel or diamond), due to its diamond-like structure. Adamantane is the most stable isomer of C₁₀H₁₆.

antane was first synthesised by Prelog

Vladimir Prelog

Vladimir Prelog was a renowned chemist and Nobel Prize winner in chemistry. Prelog lived and worked in Prague, Zagreb and Z?rich during his lifetime....
in 1941.

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Encyclopedia

Adamantane (tricyclo[3.3.1.1^3,7]decane) is a colourless, crystalline compound with a camphor

Camphor

Cycloalkane

Diamondoid

Petroleum

Synthesis

Adamantane was first synthesised by Prelog

Vladimir Prelog

Vladimir Prelog was a renowned chemist and Nobel Prize winner in chemistry. Prelog lived and worked in Prague, Zagreb and Z?rich during his lifetime....
in 1941. A more convenient method was found by Schleyer

Paul von Rague Schleyer

Paul von Ragu? Schleyer is an organic chemistry physical chemist of substantial significance whose research has been cited with great frequency....
in 1957, from dicyclopentadiene

Dicyclopentadiene

Dicyclopentadiene, abbreviated DCPD, is the chemical compound with the formula C10H12. At room temperature, it is a white crystalline solid with a camphor-like odor....
by hydrogenation

Hydrogenation

Hydrogenation is the chemical reaction that results from the addition of hydrogen . The process is usually employed to a redox or Saturation organic compounds....
followed by acid-catalysed skeletal rearrangement.

Uses

Adamantane itself enjoys few applications since it is merely an unfunctionalised hydrocarbon

Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons, whereas other hydrocarbons with bonded com...
. It is used in some dry etching

Dry etching

Dry etching refers to the removal of material, typically a masked pattern of semiconductor material, by exposing the material to a bombardment of ions that dislodge portions of the material from the exposed surface....
masks. It is also used in some polymer

Polymer

A polymer is a large molecule composed of repeating structural units typically connected by covalent chemical bonds. While polymer in popular usage suggests plastic, the term actually refers to a large class of natural and synthetic materials with a variety of properties....
formulations.

In solid-state NMR spectroscopy, adamantane is a common standard for chemical shift

Chemical shift

In nuclear magnetic resonance , the chemical shift describes the dependence of nuclear magnetic energy levels on the electronic environment in a molecule....
referencing.

In dye laser

Dye laser

A dye laser is a laser which uses an organic compound dye as the lasing medium, usually as a liquid solution. Compared to gases and most solid state lasing media, a dye can usually be used for a much wider range of wavelengths....
s, adamantane may be used to extend the life of the gain medium; it cannot be photoionised

Photoionisation

Photoionisation is the physical process in which an incident photon ejects one or more electrons from an atom, ion or molecule.The ejected electrons, known as photoelectrons, carry information about their pre-ionised states....
under atmosphere because its absorption bands lie in the vacuum-ultraviolet region of the spectrum. Photoionization energies have been determined recently for adamantane as well as for several bigger diamondoids.

Adamantane derivatives

Adamantane derivatives are useful in medicine, e.g. amantadine

Amantadine

Amantadine is the organic compound known formally as 1-aminoadamantane. The molecule consists of adamantane backbone that is substituted at one of the four methyne positions with an amino group....
, memantine

Memantine

Memantine is the first in a novel class of Alzheimer's disease medications acting on the glutamatergic system by blocking NMDA glutamate receptors....
and rimantadine

Rimantadine

Rimantadine is an orally administered antiviral drug used to treat, and in rare cases prevent, Influenzavirus A infection. When taken within one to two days of developing symptoms, rimantadine can shorten the duration and moderate the severity of influenza....
. Condensed adamantanes or diamondoid

Diamondoid

A diamondoid, in the context of building materials for nanotechnology components, most generally refers to structures that resemble diamond in a broad sense: namely, strong, stiff structures containing dense, 3-D networks of covalent bonds, formed chiefly from first and second row atoms with a valence of three or more....
s have been isolated from petroleum fractions, where they occur in small amounts. These species are of interest as molecular approximations of the cubic diamond framework, terminated with C-H bonds. 1,3-Dehydroadamantane is a member of the propellane

Propellane

Propellanes are a class of bicyclic molecule organic compounds sharing a common carbon-carbon bond. They are characterized by the presence of carbon with an inverted tetrahedral geometry, large steric strain and high reactivity and are for these reasons much studied in organic chemistry....
family.

Due to its stability, specific steric properties and conformational rigidity, the 1-adamantyl group is a (bulky) substituent

Substituent

In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. The suffix -yl is used when naming organic compounds that contain a substituent....
in organic

Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
and organometallic chemistry

Organometallic chemistry

Organometallic chemistry is the study of chemical compounds containing chemical bonding between carbon and a metal. Since many compounds without such bonds are chemically similar, an alternative may be compounds containing metal-element bonds of a largely covalent character....
. Some of the first persistent carbene

Persistent carbene

A persistent carbene is a type of carbene demonstrating particular stability despite also being a reactive intermediate. The instability in these carbenes involves reactivity with Substrate s, or dimerisation ....
s featured adamantyl substituents.

Adamantane analogues

Many molecules adopt cage structures with adamantanoid structures. Particularly useful compounds with this motif include P₄O₆, As₄O₆, P₄O₁₀ (= (PO)₄O₆), P₄S₁₀ (= (PS)₄S₆)

Phosphorus pentasulfide

Phosphorus pentasulfide is the chemical compound with the formula P4S10. This yellow solid is an industrially important inorganic compound of phosphorus and sulfur....
, and N₄(CH₂)₆.