166540-14-3Relevant articles and documents
Stereochemistry of 2-Methyl- and 2-Phenyl-2-adamantyl Cations
Herrmann, Roland,Kirmse, Wolfgang
, p. 699 - 702 (2007/10/02)
When both diastereomers of -2-methyl-2-adamantyl 2,4-dinitrophenolate (18a) and -2-phenyl-2-adamantyl 2,4-dinitrophenolate (18b) were solvolyzed in 40percent aqueous acetone, 1:1 mixtures of (E)- and (Z)--2-R-adamantan-2-ols (19a, b) were obtained.The stereoselectivity of secondary 2-adamantyl cations, attributed to ? participation, is effectively suppressed by charge-stabilizing groups at C-2. - Key Words: Solvolysis / ? Participation / 5-D-2-Adamantyl derivatives