Adamantane

Description

Adamantane (formally tricyclo[3.3.1.13,7]decane) is an exquisitely symmetrical hydrocarbon that was originally isolated from petroleum in 1933 by the Czech researchers S. Landa and V. Machacek. Its synthesis was first reported by Vladimir Prelog in 1941. It’s the simplest diamondoid compound and is nice to look at, but it has few practical applications.

Chemical properties

slightly beige crystals

The Uses of Adamantane

Adamantane is mainly used for the synthesis of medicine to treat influenza, serve as NMDA receptor channel blockers. Also be used for preparation of advanced lubricants, photographic material, surface active agents, catalysts and other products.

The Uses of Adamantane

synthon for Amantadine, Rimantadine, Somantadine, Tromantadine

The Uses of Adamantane

The diamine as curing agent for epoxy resins [US 3053907 (1962 to du Pont)].

Definition

adamantane: A colourless crystallinehydrocarbon C₁₀H₁₆; m.p.269°C. It is found in certain petroleumfractions. The structure containsthree symmetrically fusedcyclohexane rings.

Synthesis Reference(s)

Journal of the American Chemical Society, 91, p. 6779, 1969 DOI: 10.1021/ja01052a041
The Journal of Organic Chemistry, 51, p. 3038, 1986 DOI: 10.1021/jo00365a034

Purification Methods

Crystallise adamantane from acetone or cyclohexane, and sublime it in a vacuum below its melting point [Butler et al. J Chem Soc, Faraday Trans I 82 535 1986]. Adamantane is also purified by dissolving it in n-heptane (ca 10mL/g of adamantane) on a hot plate, adding activated charcoal (2g/100g of adamantane), and boiling for 30minutes, filtering the hot solution through a filter paper, concentrating the filtrate until crystallisation just starts, adding one quarter of the original volume of n-heptane, and allowing to cool slowly over a period of hours. The supernatant is decanted off and the crystals are dried in vacuo at 25o. [Prelog & Seiwerth Chem Ber 74 1769 1941, Schleyer et al. Org Synth Coll Vol V 16 1973, Walter et al. J Am Chem Soc 107 793 1985.] [Beilstein 5 III 393, 5 IV 469.]