We talk about Adamantane

12/31/2013 16:48

Adamantane is the generic name for a family of derivatives Idemitsu has developed based on adamantane, whose functional group provides the advantages of the adamantane framework in a range of materials.

By using Adamantane as a base resin, Idemitsu can introduce superior adamantane characteristics such as heat resistance, stiffness and transparency for a variety of products including flat panel displays and semiconductor manufacturing photoresists.

Pure adamantane(CAS NO: 281-23-2) is a colorless crystalline solid with a characteristic camphor smell. It is practically insoluble in water, but readily soluble in nonpolar organic solvents. Adamantane has an unusually high melting point for a hydrocarbon.

At 270 C, its melting point is much higher than other hydrocarbons with the same molecular weight, such as camphene (45 C), limonene (–74 C), ocimene (50 C), terpinene (60 C) or twistane (164 C), or than a linear C10H22 hydrocarbon decane (–28 C). However, adamantane(CAS NO: 281-23-2) slowly sublimates even at room temperature. Adamantane can distill with water vapor.

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Adamantane antivirals are only active against influenza A virus, an RNA virus, but has no action against influenza B virus. A viral membrane protein, M2, functions as an ion channel at two stages of the viral replication within the host cell. These stages are the fusion of viral membrane and endosome membrane, and the assembly and release of new virions. Adamantane antivirals block this ion channel.

The adamantane cation can be produced by reacting 1-fluoro-adamantane with SbF5 and it has high stability compared with other carbocations, even tertiary ones. The dication of adamantane was obtained in solutions of superacids. It also has elevated stability due to the phenomenon called "three-dimensional aromaticity" or homoaromaticity, This four-center two-electron bond involves one pair of electrons delocalized among the four bridgehead atoms.

Most reactions of adamantane occur via the 3-coordinated carbon sites and are described in the subsections below. The 2-coordinated, bridging carbon sites are much less reactive. They are involved in the reaction of adamantane with concentrated sulfuric acid which produces adamantanone. The carbonyl group of adamantanone allows further reactions via the bridging site. For example, adamantanone is the starting compound for obtaining such derivatives of adamantane as 2-adamantanecarbonitrile and 2-methyl-adamantane.

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