18341-84-9Relevant articles and documents
Preparation of 1-adamantyl ketones: Structure, mechanism of formation and biological activity of potential by-products
Vicha, Robert,Necas, Marek,Potacek, Milan
, p. 709 - 722 (2008/02/01)
Reactions between adamantane-1-carbonyl chloride and several Grignard reagents as well as interactions with solvents have been examined. Some new and unexpected adamantane derivatives were isolated, fully characterized and their biological activity determined. In particular, an unexpected isochromanone 16 was formed in an SEAr process, in which a stable hydrocarbon was the leaving group.
Adamantanemethanol derivatives and production processes thereof
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Example 3, (2008/06/13)
An adamantanemethanol derivative of the invention is represented by the following formula (1), wherein Rais a hydrogen atom or a hydrocarbon group; Rbis a hydrocarbon group having a carbon atom, to which carbon atom at least one hydrogen atom is bonded, at a bonding site with the adjacent carbon atom; Rc, Rdand Reare each a hydrogen atom, a hydroxyl group which may be protected by a protective group or the like; provided that a hydroxyl group protected by a protective group or the like is bonded to at least one carbon atom constituting the adamantane skeleton when Rais a hydrogen atom or a methyl group and Rbis a methyl group; and at least one substituent, in addition to the HO—C(Ra)(Rb)— group indicated in the formula (1), is bonded to the adamantane ring when one of Raand Rbis a methyl group and the other is an ethyl group.
The Mechanism of Solvolysis of 2,2-Dimethyl-3-pentyl and 1-(1-Adamantyl)propyl Sulfonates
Shiner Jr., Vernon J.,Neumann, Thomas E.,Basinger, Bradley B.
, p. 1405 - 1420 (2007/10/03)
Solvolysis rates, alpha and beta deuterium isotope rate effects and product yields have been determined for some 1-(1-adamantyl) propyl sulfonate esters, 4, in some ethanol-water, trifluoroethanol-water and hexafluoroisopropyl alcohol-water mixtures. For comparison, similar measurements have been made for solvolysis of 2,2-dimethyl-3-pentyl sulfonates, 5. For the esters 5, the alpha-d and beta-d2 effects vary little with solvent in the ranges of 1.164-1.165 and 1.215-1.241, respectively, and only small yields of unrearranged products are formed; it is concluded that the mechanism involves rate determining formation of the secondary cation-ion pair followed by rapid rearrangement. For the adamantyl analogs, 4, the alpha-d effects vary in the different solvents from 1.162 to 1.213 and the beta-d2 effects vary from 1.339 to 1.649; significant yields of unrearranged and Wagner-Meerwein rearranged (ring expansion) products are formed. The steady state treatment, which had been used previously to fit the results for 1-(1-adamantyl)ethyl esters, was applied to the results for 4; a mechanism which involves partially reversible ionization to the intimate ion-pair followed by competing elimination and solvent separation, to give the substitution products, fits the results reasonably well.