Polyfunctionalization of Cage Hydrocarbons
Abstract
This report details the work carried out at the University of Erlangen-Nuernberg aimed at the syntheses of polyhalogenated cage molecules, their isolation, characterization, and assessment as potential precursors to high density energy materials. A variety of halogenation methods have been investigated and applied (sometimes in combination) to a number of different starting materials e.g. adamantane C10H16 1, diamantane C14H10 2, and norbornadiene dimer C14H16 3. Photochlorination has been found to be the most effective method of introducing large numbers at halogens into these cage molecules and has been applied to a variety of starting materials, culminating in the synthesis of 1,3,5,7-tetrabromodecachloroadamantane 4 and the successful analysis of its structure by X-ray diffraction. This corresponds to over 87% halogenation. Relatively high degrees of functionalization (70% and 50%) have been achieved for diamantane 2 and norbornadiene dimer 3 respectively. The synthetic work as well as the methods of separation and characterization of the product mixtures are reported. The results of semi-empirical molecular orbital calculations on dodecachloroadamantanes 5 and of the X-ray structural analysis of 4 are discussed.
Document Details
- Document Type
- Technical Report
- Publication Date
- Aug 01, 1988
- Accession Number
- ADA202389
Entities
People
- Paul Von Rague Schleyer