page_title: Diamantane
section_title: Occurrence and history
hierarchical_section_title: Diamantane / Occurrence and history
caption_attribution_description: English: Diamondoids
context_page_description: Diamantane is an organic compound that is a member of the diamondoids. These are cage hydrocarbons with structures similar to a subunit of the diamond lattice. It is a colorless solid that has been a topic of research since its discovery in oil and separation from deep natural gas condensates. Diamondoids such as diamantane exhibit unusual properties, including low surface energies, high densities, high hydrophobicities, and resistance to oxidation.
context_section_description: Diamantane occurs naturally in crude petroleum. It is currently assumed that adamantanes and diamantanes were formed via the catalytic rearrangements of polycyclic naphthenic hydrocarbons. Although present in only trace concentrations in typical oils, due to their great thermodynamic stability, diamondoids such as diamantane are naturally concentrated by catagenesis, becoming important constituents of some natural gas condensates including those from the Norphlet Formation, U.S. Gulf of Mexico, and the Western Canada Basin.
  Diamantane was chosen as the Congress Emblem of the 1963 London IUPAC meeting, and was featured as a decoration on the
  cover of abstracts, program, and publicity material. Congress participants were challenged to synthesize diamantane. The first preparation of this chemical was achieved in 1965 in 1% yield by aluminum halide-catalyzed isomerization of a mixture of norbornene photodimers. Adamantane was the first, and "Congressane", as diamantane came to be known, was only the second member of an entire family of compounds known as the diamandoids. The synthesis of the third member of the series in 1969 emphasized the need for a more general scheme of semitrivial nomenclature. The compound was renamed "diamantane" and the third member designated "triamantane".
  The year 1966 also marked the isolation of diamantane from the high-boiling fractions of the crude oil of Hodonin (from which adamantane was discovered) and the achievement of a significant improvement in its yield (to 10%). While this permitted a start to be made in the exploration of the chemistry of diamantane, the hydrocarbon was still difficult to obtain in quantity. Diamantane then became as readily available as adamantane and its chemistry could be studied more easily.
caption: Diamantane is the second member of this series of diamondoid hydrocarbons.
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