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Facile Synthesis of 3-(Azol-1-yl)-1-adamantanecarboxylic Acids-New Bifunctional Angle-Shaped Building Blocks for Coordination Polymers.

ABSTRACT: For the first time, orthogonally substituted azole-carboxylate adamantane ligands were synthesized and used for preparation of coordination polymers. The angle-shaped ligands were prepared by the reaction of 1-adamantanecarboxylic acid and azoles (1H-1,2,4-triazole, 3-methyl-1H-1,2,4-triazole, 3,5-dimethyl-1H-1,2,4-triazole, 1H-tetrazole, 5-methyl-1H-tetrazole) in concentrated sulfuric acid. Variation of the solvent and substituents in azole rings allowed to prepare both 1D and 2D copper(II) and nickel(II) coordination polymers, [Cu2(trzadc)4(H2O)0.7]?DMF?0.3H2O, [Cu(trzadc)2(MeOH)]?MeOH, [Ni(trzadc)2(MeOH)2] and [Cu2(mtrzadc)3(MeOH)]+NO3- (trzadc-3-(1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid; mtrzadc-3-(3-methyl-1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid) which were structurally characterized by single crystal X-ray diffraction. Complex [Cu(trzadc)2(MeOH)]?MeOH was shown to act as a catalyst in the Chan-Evans-Lam arylation reaction.

SUBMITTER: Pavlov D 

PROVIDER: S-EPMC6695720 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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Facile Synthesis of 3-(Azol-1-yl)-1-adamantanecarboxylic Acids-New Bifunctional Angle-Shaped Building Blocks for Coordination Polymers.

Pavlov Dmitry D   Sukhikh Taisiya T   Filatov Evgeny E   Potapov Andrei A  

Molecules (Basel, Switzerland) 20190726 15

For the first time, orthogonally substituted azole-carboxylate adamantane ligands were synthesized and used for preparation of coordination polymers. The angle-shaped ligands were prepared by the reaction of 1-adamantanecarboxylic acid and azoles (1<i>H</i>-1,2,4-triazole, 3-methyl-1<i>H</i>-1,2,4-triazole, 3,5-dimethyl-1<i>H</i>-1,2,4-triazole, 1<i>H</i>-tetrazole, 5-methyl-1<i>H</i>-tetrazole) in concentrated sulfuric acid. Variation of the solvent and substituents in azole rings allowed to pr  ...[more]

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