Chemistry of Adamantanes by R.C. Bingham, P.R.v. Schleyer

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

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

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15o). Cf Ref. 155)). l-adamantyl cation appear furthest downfield. This "anomalous" chemical shift is also observed in the spectrum of the i-diamantyl cation (58) obtained from the SbFs-FSO3H solution of diamantane 157). 67 ppm 58 This 7-deshielding effect might be explained on the basis of a special cage effect which enables the back lobes of the bridgehead C-H bonds to overlap with the vacant p-orbital of the cation 156). No direct experimental evidence exists which would substantiate this special cage effect, however.

0 4, 1o]. decanol (Eq. (28)) 9a). NNTs Na + (27) 29 0 (28) 42 Direct substitution of hydrocarbon 2 9 via both carbomethyloxynitrene insertion (Eq. (29)) and chromyl acetate oxidation (Eq. (30)) has been studied. The nitrene insertions are fairly unselective. On a per bond basis, both tertiary NHCO2 CH3 29 9 N H C O ~ CH 3 + (29) + 120 ~ NHCO2CH 3 OH , ยง (30) sites are attacked about 4 times more readily than the methylene positions. Tertiary/secondary ratios of this order are quite typical 94).

A. 100 MHz spectrum of triamantane. B. 220 MHz spectrum of homoadamantane. (After Ref. 33) and 1S 1), respectively). 43 Physical Properties duced in the mono-substituted adamantanes, the chemical shifts of a wide variety of 1,3-, 1,3,5. and 1,3,5,7-polysubstituted adamantanes may be estimated accurately. The chemical shifts of 1-substituted adamantanes are correlated well with substituent electronegativity 15o) as measured by o* 152) or group dipole moments 153) Only the chemical shifts observed for the 7 (bridgehead) position exhibit the normal inductive order, however; the chemical shifts of the/~ (adjacent methylene) and 8 (far methylene) hydrogens appear to be anisotropy controlled 159).

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