Advances in the Chemistry of Organic Ring Systems with Adamantane Type Structures

Abstract

Since the last review of the topic in 1954 [l], the chemistry of organic compounds with the adamanrane type structures has been considerably advanced in scope and significance by the work of the author and of others. Since 1954, the number of ring systems of this type known has risen from 13 to 22. At the same time, the number of compounds with adamantane type structures known has been more than tripled. Summary of recent advances is therefore justified. As before, the emphasis in this review is placed on complete coverage.

Synthesis of Six and Seven-membered Heterocyclic Molecules Containing an Adamantyl Fragment and an X-ray Crystal Structure of (E)-N-(adamantan-1-yl)-1-(3-nitrophenyl)methanimine

“…The adamantyl group has been found to be an important component in the development of many drug treatments (3). For example, the addition of adamantyl moiety to an active pharmaceutical molecule leads to improvements in an array of therapeutic drugs (4), and adamantan-1-ylamine was the first anti-viral treatment to be developed (5). This development led to the synthesis and testing of hundreds of adamantylamine derivatives for different bioactivities, especially for cancer drugs.…”

Evaluation of the Spacer Effect on Adamantane-Containing Vinyl Polymer Tg's

“…Polymers having adamantane as a pendant group or in the backbone show enormous changes in their physical and chemical properties. [2][3][4] Our group has been studying the effects of adamantane substitution on physical, thermal, and mechanical properties of a variety of polymer families ranging from acrylates to phenolics. 5 Incorporation of adamantane as a pendant group increases the T g of the parent polymer significantly for both condensation polymers and vinyl polymers.…”

“…This compound is thermodynamically very stable, plus it has unusual effects on polymer behavior. Polymers having adamantane as a pendant group or in the backbone show enormous changes in their physical and chemical properties. − Our group has been studying the effects of adamantane substitution on physical, thermal, and mechanical properties of a variety of polymer families ranging from acrylates to phenolics . Incorporation of adamantane as a pendant group increases the T g of the parent polymer significantly for both condensation polymers and vinyl polymers. ,− Although it is intuitive that large pendant groups tend to have such an effect due to the reduced chain mobility (boat anchor effect), the magnitude of increase is surprisingly high for adamantane.…”

Catalysts Containing the Adamantane Scaffold

“…bromo 3 and alcohol 4 derivatives; both obtainable in 95% from 1). [6] Since this time, the adamantane scaffold has seen extensive application. Notably within the context of this review, the desirable properties that adamantane provides to catalyst development include, inert hydrocarbon reactivity, rigidity and symmetry, and steric bulk.…”