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By R.C. Bingham, P.R.v. Schleyer

Content material: contemporary advancements within the chemistry of adamantane and similar polycyclic hydrocarbons / by way of R.C. Bingham and P.V.R. Schleyer

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Extra resources for Chemistry of Adamantanes

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Solvolysis reactions at the 10-position are known to be highly unfavorable 95). 0 4, 10] decyl tosylate is retarded relative to 1-adamantyl tosylate by a factor of approximately 106 at 70~ in acetic acid. 29 Synthesis and Chemistry of Polycyclie Hydrocarbons Related to Adamantane D. Homoadamantanes 1. Ring Expansions of Adamantane Homoadamantane derivatives are most readily obtained from ring expansions of appropriately substituted adamantanes. Carbonium ion reactions ofadamantylcarbinyl systems have long been known to give 3-homoadamantyl derivatives as the major product 4).

578 25 59 60 61 Table 7. F 19 chemical shifts o f bridgehead fluorides 175) Compound ~ ~ ~ F 19 chemical shift a) F 132 148 F F 194 a) In CC14 relative to external CC13F. 49 Physical Properties milar interaction in 1,1'-binorbornane might contribute to the shortened central C-C bond of this compound. Substituent effects on the F 19 chemical shifts of bridgehead adamantyl fluorides also show unexpected trends. A shielding effect is observed for both 3-methyl- 1-adamantyl fluoride 176) and 3-carbomethoxy- 1-adamantyl fluoride.

The 57 Chemical Properties strain introduced by the axial-t-butyl substituent described above must be quite large. -butyl-2-adamantanol by t-butyl lithium addition to adamantanone is observed 208). Obviously, additions to the carbonyl function of adamantanone may be expected to be of general utility. Introduction of functional groups to the adamantane nucleus after the hydrocarbon itself has been prepared is clearly a general and useful approach for the preparation of a wide variety of adamantane derivatives.

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