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Adamantane is the saturated cage hydrocarbon ${\mathrm{C}}_{10}{\mathrm{H}}_{16}$. Its carbon framework is a compact three-dimensional network of fused chair-like six-membered rings, with the connectivity recorded by its tricyclic structural name.^[ref]

The rigid cage restricts conformational motion. Symmetry can make several carbon or hydrogen positions equivalent in a spectrum, while substitution breaks those equivalences. The molecule therefore provides a useful example of how three-dimensional connectivity and molecular symmetry influence chemical reactivity and spectroscopic counting.

Paul von Ragué Schleyer developed a short preparation of adamantane, a cage-shaped hydrocarbon, and became a major contributor to computational chemistry. His 1957 report illustrates how rearrangement reaction can turn a different carbon skeleton into a highly symmetrical cage.^[ref]