Abstract
The symmetric bridge disubstituted adamantane derivatives are the key raw materials or intermediates for preparing multisubstituted adamantane derivatives with admantane as the core. With 1-adamantane carboxylic acid that is more efficient and economical as an initial reactant, a series of synthesis technologies of symmetrical disubstituted bridgehead adamantane derivatives which have significant applications, were studied in this work. Those synthesis technologies include the following: 1,3-adamantane dicarboxylic acid (1) was synthesized by 1-adamantane carboxylic acid through Koch-Haaf carbonylation; compound 1 was reduced to get 1,3-adamantane dimethanol(2); compound 2 reacted by bromination in HBr-ZnBr2 system to afford 1,3-dibromomethyl adamantane(3). Meanwhile, compound 2 converted to 1, 3-dichloromethyl adamantane (4) through Apple-Lee reaction. The structures of prepared products were confirmed by IR spectra and H-1 NMR spectroscopy. The possible reaction mechanism was proposed, and the synthesis conditions were discussed and optimized for each technology respectively.
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