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N-(Het)arylation of adamantane-containing amines with halonaphthalenes and haloquinolines catalyzed by either CuI or copper nanoparticles with an average size of 25 nm in the presence of 2-isobutyrylcyclohexanone, rac-BINOL, and l-proline as a ligand and Cs2CO3 as a base in DMSO at 110 °C was studied. The reactions proceed smoothly with 2-iodonaphthalene and 6-iodoquinoline, the possibility of successful reactions with 6- and 3-bromoquinolines was also shown. In the case of 1-bromonaphthalene, 5- and 8-bromoquinolines, only Pd-catalyzed amination can provide the high yields of the products. An alternative possibility of C(sp2)—N bond formation was studied employing the Chan—Lam reaction with of 2-naphthaleneboronic acid and pinacolates of 6- and 3-quinolineboronic acids. [ABSTRACT FROM AUTHOR]

Optically transparent polyimides (PIs) containing adamantane moieties in the structure of diamine unit were synthesized, and their properties were evaluated. The quantum-chemical calculations were also performed and revealed the energy difference (As) between the HOMO of the diamine and LUMO of the anhydride moieties for a large range of adamantane-containing PIs, which is usually associated with the optical absorption of organic compounds. It was found that the value of As does not always determine the optical properties of PI, especially in the case of PI with dianhydride moieties capable of strong intermolecular interactions. The presence of methyl groups at the core of adamantane-containing diamine leads to amorphization of the polymer, causing a positive effect on the optical properties of PI. [ABSTRACT FROM AUTHOR]

Alkylation of N-aryl and N-arylalkyl acetamides with hydroxy adamantane derivatives in trifluoroacetic acid was studied. The differentiating effect of trifluoroacetic acid on the regio-selectivity of adamantylation of o-alkyl-substituted acetanilides was established, leading to energetically more stable products of para-substitution with respect to the alkyl group (the content of para-alkyl isomers is 93–94%). This enabled the synthesis of adamantylaminoarenes in 83–99% yields and with 95–99% purity. [ABSTRACT FROM AUTHOR]