Synthesis of Rigid Tetrahedral Tetrafunctional Molecules From 1,3,5,7-Tetrakis(4-Iodephenyl)adamantane
Polymers and High Performance Materials
1,3,5,7-Tetrakis(4-iodophenyl)adamantane was prepared from 1-bromoadamantane in overall yields of ca. 50%. Conversion to several derivatives occurred in good yields: palladium-catalyzed coupling with 2-methyl-3-butyn-2-ol followed by deprotection gave the tetrakis(phenylacetylide), and reaction with phenyl boronic acid gave the tetrakis(biphenyl)adamantane with all-para linkages. The tetrakis(4-iodophenyl) adamantane offers broad potential for synthesis of star, dendritic, and hyperbranched structures with enforced tetrahedral symmetry derived from the rigid adamantane core.
Chemistry of Materials
Mathias, L. J.,
Reichert, V. R.,
Muir, A. V.
(1993). Synthesis of Rigid Tetrahedral Tetrafunctional Molecules From 1,3,5,7-Tetrakis(4-Iodephenyl)adamantane. Chemistry of Materials, 5(1), 4-5.
Available at: http://aquila.usm.edu/fac_pubs/6390