772-26-9Relevant academic research and scientific papers
Selective hydroxylation of adamantane and its derivatives
Khusnutdinov,Shchadneva,Mukhametshina,Dzhemilev
scheme or table, p. 1137 - 1142 (2009/12/03)
A general method was developed for hydroxylation into the nodal position of adamantane and its 1- and 2-substituted derivatives employing systems H 2O-CBr4 (BrCCl3, CCl4) in the presence of complexes of Pd, Ni, Ru, Co, Mo, W, and Fe. The oxidants in the systems are hypochlorous (HOCl) or hypobromous (HOBr) acids generated from water and halomethanes under the reaction conditions.
Molecule-induced alkane homolysis with dioxiranes
Fokin,Tkachenko,Korshunov,Gunchenko,Schreiner
, p. 11248 - 11252 (2007/10/03)
The mechanisms of C-H and C-C bond activations with dimethyldioxirane (DMD) were studied experimentally and computationally at the B3LYP/6-311+G**//B3LYP/6-31G* density functional theory level for the propellanes 3,6-dehydrohomoadamantane (2) and 1,3-dehydroadamantane (3). The σC-C activation of 3 with DMD (ΔG? = 23.9 kcal mol-1 and ΔGr = -5.4 kcal mol-1) is the first example of a molecule-induced homolytic C-C bond cleavage. The C-H bond hydroxylation observed for 2 is highly exergonic (ΔGr = -74.4 kcal mol-1) and follows a concerted pathway (ΔGr = 34.8 kcal mol-1), in contrast to its endergonic molecule-induced homolysis (ΔG? = 28.8 kcal mol-1 and ΔGr = +9.2 kcal mol-1). The reactivities of 2 and 3 with CRO2Cl2, which follow a molecule-induced homolytic activation mechanism, parallel the DMD results only for highly reactive 3, but differ considerably for more stable propellanes such as 4-phenyl-3,6-dehydrohomoadamantane (1) and 2.
Herstellung und Solvolyse von 3-substituierten p-Toluolsulfonsaeure-(1-adamantyl)estern
Bielman, Rolf,Grob, Cyril A.,Schaub, Bruno
, p. 1728 - 1733 (2007/10/02)
Methods for the preparation of some hitherto unknown 3-substituted 1-adamantyl toluenesulfonates are evaluated.Their solvolysis products in dioxane/water 70:30 are reported.
