24813-21-6Relevant articles and documents
A new route to N-(1-adamantyl)nicotinamide
Sokolenko,Svirskaya,Pavlenko
, p. 331 - 332 (2006)
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Cavitand-porphyrins
Starnes,Rudkevich,Rebek, Jr.
, p. 4659 - 4669 (2007/10/03)
The synthesis and characterization of new nanoscale container molecules 7 and 8 are described. They are covalent hybrids of deepened, self-folding cavitands and metalloporphyrins. In receptor 7, the Zn-porphyrin wall is directly built onto the cavitand skeleton. Host 8 features a large unimolecular cavity containing two cavitands attached with the Zn-porphyrin wall. Its dimensions, ~10 × 25 A, place it among the largest synthetic hosts prepared to date. A series of adamantyl- and pyridyl-containing guests 14-20 of various lengths were prepared and used to determine the hosts' binding abilities in solution using UV/vis and 1H NMR spectroscopy. Intramolecular hydrogen bonds at the upper rims of the cavitands resist the unfolding of the inner cavities and thereby increase the energetic barrier to guest exchange. The exchange is slow on the NMR time scale (at ≤300 K), and kinetically stable complexes result. When the cavities and metalloporphyrins participate simultaneously in the binding event, very high affinities for guests are found (-ΔG295 up to 10 kcal mol-1 in toluene), to which the porphyrin fragments contribute significantly (-ΔG295 up to 6 kcal mol-1). The pairwise selection of two different guests by molecular container 8 is reported, and the termolecular complex formed raises the possibility of metal-catalyzed bimolecular reactions in these containers.
Adamantylation and adamantylalkylation of amides, nitriles and ureas in trifluoroacetic acid
Shokova, Elvira,Mousoulou, Tasoulla,Luzikov, Yurij,Kovalev, Vladimir
, p. 1034 - 1040 (2007/10/03)
A new preparative method for N-adamantylation of carboxylic acid amides, ureas and for C5-adamantylation of barbituric acid in trifluoroacetic acid (TFA) is proposed. Tertiary 1-adamantanols and 1-(1-adamantyl)alkanols were used as adamantylating agents. The reaction of 1-(1-adamantyl)alkanols with nitriles in TFA solution was employed for the first time for the preparation of N-[1-(1-adamantyl)alkyl]amides.