Hydroxy Derivatives of Diamantane, Triamantane, and [121]Tetramantane: Selective Preparation of Bis-Apical Derivatives†

Functionalizations of diamantane, triamantane, and tetramantane with electrophilic reagents (Br2, nitric acid) lead to various apical and medial disubstituted products that were separated and characterized individually. The highly desirable and otherwise inaccessible thermodynamically more stable apical bis-derivatives were obtained with high preparative yields through acid catalyzed isomerizations. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)