Before its discovery, adamantane was known as decaterpene, the name applied by Decker to his tricyclic hydrocarbon. Decker believed that his decaterpene was similar in structure as the diamond lattice. Decaterpene, as in diamond, was proposed by Decker to be highly structured and strain free.2

Decker proposed decaterpene in 1924, but that was all it was until 1933 when the structure was proven to exist. Isolated in the petroleum of Hodinin, Czechoslovakia by Landa and Machachaeck, decaterpene became incarnate.3 However, the fact that they found the structure Decker predicted did not mean that his nomenclature would be used to identify the compound. That honor was bestowed upon its discoverers Landa and Machcahcaeck who used the Gr

10. Ege, Seyhan. Organic Chemistry: Structure and Reactivity. 3rd ed. D.C. Heath and Co.: Lexington, MA. 1994.

Now that the natural product has been discovered, the next logical step would be to formulate the natural process in which the compound was made. As of 1964, the natural method that creates the adamantane compound had not been found. The natural process that was attempted was to bombard adamantane-free petroleum with catalysts in an attempt to initiate the formation of adamantane. The resulting mixture was fractioned and analyzed to see if any extra adamantane was created. In most cases, the catalyst failed to produce any adamantane. However, many of the catalysts produced derivatives that had the ring structure but with extra components attached.5 The only catalyst shown to make a significant amount was AlCl3, but not enough was created for the catalyst to be considered for mass production of adamantane. Catalysts that failed were: oil-bearing stone from Hodin with and without HF, aluminum silicate, aluminum oxide, concentrated sulfuric acid, zinc chloride, iron(III) chloride, tin(IV) chloride, antimony(V) chloride.5 It is believed that the reason many of the catalysts did not work, even though they are present in natural petroleum, is that the conditions that they were subjected to were experimental in nature. The creation of adamantane is thought to be a biogenesis of petroleum under a set of conditions that is not able to be recreated in the lab.2

When Schleyer focused his procedure on the retrieval of adamantane, he found that the synthesis was bountiful with the starting reactant dicyclopentadiene which is a common compound.3 Research into the enigmatic compound could then proceeded full force from this point on to examine the compound to its every minute detail. What they found confirmed their previous assertions that adamantane was unlike any carbohydrate known to man.

Since adamantane is so symmetrical and stable, it becomes the perfect basis for many studies and research. In fact the universality of adamantane is so great that it is capable of being used for: structure reactivity relationships, development of empirical force field methods, orientation disorder probe model, and structure basis for drugs.5 The possibilities are endless for adamantane and its uses simply because of its simplicity in nature and structure allow for a structure that is one of the most unique and strong in nature.

The only problem with the fractional distillation method is that adamantane cannot be extracted in large quantities because it exists in only a small quantity in petrol. The presence of adamantane was found to be only 0.0004% of the composition of petroleum by the fractional distillation method.2 Adamantane is not alone in the petroleum distillate in which it is present. Alkylated adamantane derivatives also show up in adamantane containing distillate. (II, III, IV) The output of adamantane is capable of being increased if the thiourea adduct method is employed on the petroleum. Landa and Hale were able to isolate complexes of adamantane from crude petroleum that had bonded to thiourea.5

3. P. von Rague Schleyer, J. Am. Chem. Soc., 79, 3292 (1957)

Before adamantane was known to the world, the starting material commonly used to synthesize adamantane and its derivatives through ring closure was being developed. In 1922, Meerwein was investigating a way to remove the bridgehead carboxymethoxy group of ring compounds, and reseal the ring structure with diiodomethane(V) and sodium. His experiments failed because the malonic ester(VI) which he created forced the reactant groups too far apart for the recycling to occur.3,4 Despite his failures, Meerwein was able to inspire other advancements

Some common words found in the essay are:
Prelog Seiworth's, NMR IRFig, Hodin HF, Machcahcaeck Greek, Landa Hale, , Prelog Seiworth, Starting Meerwein's, Landa Machachaeck, III IV, fractional distillation, prelog seiworth, output adamantane, ring closure, ring structure, schleyer chem, adamantane synthesis, method adamantane, temperature column decreases, adamantane capable, adamantane derivative,
Approximate Word count = 2525
Approximate Pages = 10 (250 words per page double spaced)