Organic reactions on the surface of alumina

Two different organic reactions are studied: first, the exchange of protium for deuterium on phenylacetylene using deuterated alumina and, second, the bromination reactions of certain cyclic and acyclic olefins on the surface of alumina.

The study of the preparation and reaction of deuterated alumina involved development of the process for dehydration and deuteration using a vacuum dehydration apparatus as well as the exchange of acidic hydrogens on organic compounds. It was found that, after six exchange cycles, deuterated alumina would yield 99% deuterated phenylacetylene after reacting as a slurry in pentane.

The reaction of bromine with an olefin was carried out by adsorbing Br₂ in CCl₄ onto dehydrated alumina and reacting with olefin adsorbed alumina. The reaction of cyclohexene on alumina yielded, in addition to trans-1,2-dibromocyclohexane, trans-1-bromo2-chlorocyclohexane. Additional products were formed for larger ring systems as well as acyclic compounds. These products included vinyl bromides of cis- and trans-2-hexene, cycloheptene and cyclooctene and an allyl chloride of cyclooctene.