Über die Synthese des Adamantans

Prelog, V.; Seiwerth, Rativoj

doi:10.1002/cber.19410741004

Cited by 102 publications

(59 citation statements)

References 5 publications

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“…Adamantane (1) was first prepared by Prelog and Seiwerth in 1941. [36] In 1957 Schleyer published a simple preparation of 1 through a so-called stabilomeric rearrangement of tetrahydrodicyclopentadiene by Lewis acids. [37] This chemistry has already been well reviewed.…”

Section: Origin and Synthesis Of Diamondoidsmentioning

confidence: 99%

Diamonds are a Chemist's Best Friend: Diamondoid Chemistry Beyond Adamantane

2008

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Marilyn Monroe knew that "diamonds are a girl's best friend" but, in the meantime, many chemists have realized that they are also extremely attractive objects in contemporary chemistry. The chemist's diamonds are usually quite small (herein: nanometer-sized "diamondoids") and as a result of their unique structure are unusual chemical building blocks. Since lower diamondoids (up to triamantane) have recently become available in large amounts from petroleum and higher diamondoids (starting from tetramantane) are now also accessible from crude oil new research involving them has begun to emerge. Having well-defined structures makes these cage compounds so special compared to other nanometer-scale diamonds. Selective and high-yielding synthetic approaches to the functionalization of diamondoids gives derivatives that can find applications in, for example, polymers, coating materials, drugs, and molecular electronics.

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Section: Origin and Synthesis Of Diamondoidsmentioning

confidence: 99%

Diamonds are a Chemist's Best Friend: Diamondoid Chemistry Beyond Adamantane

2008

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“…It is known that a non-planar sequence of three lines on the diamond lattice is chiral. [8,9] Indeed, taking as an example the tetramantanes, and ignoring the branched [1(2)3]tetramantane, there are two isomeric regular non-branched tetramantanes: the achiral zigzag [121]tetramantane whose dualist is a z-like coplanar sequence of three equal lines, and the chiral [123]tetramantane with a nonplanar dualist In the former case one may continue lengthening the dualist in a self-similar manner resulting in a quasilinear zigzag poly[12…]catamantane which is examined in detail in the following. However, in the latter case, there are two possibilities: (i) lengthening the dualist by repeating the 123 triplet, which leads to cancellation of chirality yielding an irregular poly[123…]catamantane; and (ii) adding a fourth direction in a self-similar manner, which leads to a regular, helical and chiral poly[1234…]catamantane.…”

Section: Introductionmentioning

confidence: 99%

Energies for Cyclic and Acyclic Aggregations of Adamantane Sharing Six-membered Rings

Balaban¹,

Ortiz²,

Klein³

et al. 2016

Croat. Chem. Acta

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Abstract:Tension energies for acyclic and cyclic assemblies of adamantane units sharing hexagons of carbon atoms converge in a size-extensive manner for large numbers n of adamantane units. In most cases the convergence features diagrams of strain energy per adamantane unit E (n -1 ) versus n -2 for cyclic aggregates and versus n -1 for acyclic aggregates having linear dependence with slopes of opposite signs. However, we found two exceptions which are discussed in the present paper, with convergence involving linear dependence with slopes of the same sign.

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“…The first and simplest member of the diamondoids group, adamantane, is a tricyclic saturated hydrocarbon (tricyclo[3.3.1.1]decane). Adamantane nucleus was first built up by Prelog and Seiwerth in 1941 via aluminum chloride-catalyzed isomerization of tetrahydrodicyclopentadiene 5 , this chemical synthesis was latterly improved via catalytic hydrogenation of dicyclopentadiene in the presence of aluminum chloride 6 . The unique structure of adamantane is reflected in its highly unusual physical and chemical properties, which can have many applications including drug design and drug delivery.…”

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confidence: 99%