29542-65-2Relevant academic research and scientific papers
Solvolysis of 2-adamantyl ONN-azoxytoluene-p-sulphonate. A new reaction
Maskill,Murray-Rust, Peter,Thompson, John T.,Wilson, Alan A.
, p. 788 - 789 (1980)
The first secondary alkyl azoxyarenesulphonate 2-adamantyl azoxytosylate, has been made and shown to have the Z configuration about the nitrogen-nitrogen double bond, rates of solvolysis and activation parameters in aqueous ethanol, aqueous trifluoroethanol and aqueous hexafluoropropan-2-ol have been determined and a solvolytic mechanism involving unimolecular fragmentation and carbonium ion intermediates is proposed.
Solvolysis of 2-Adamantyl Trifluoromethanesulfonate : A YOTf Scale
Kevill, Dennis N.,Anderson, Steven W.
, p. 3330 - 3333 (1985)
The solvolysis of 2-adamantyl trifluoromethanesulfonate proceeds at a convenient rate at temperatures below ambient in a wide variety of pure and aqueous organic solvents and in ethanol-2,2,2-trifluoroethanol mixtures.A scale of Grunwald-Winstein Y values (YOTf) is developed for 26 solvents and it is found to much more closely resemble the corresponding yOClO3 scale than the corresponding scale of YOTs values.In aqueous ethanol, there is a preference for product formation by interaction with water molecules by a factor of ca. 1.5, essentially independent of solvent composition (96-50percent ethanol).
Stereochemistry and Mechanism of ?-Assisted Solvolysis of endo-Bicyclonon-6-ene-3-methyl Tosylate
Nordlander, J. Eric,Kotian, Kirtivan D.,Raff, Dwight E.,Grohol, William P.,Vishwanath, Vasanth M.,Winemiller, Jeffry J.
, p. 863 - 867 (2007/10/02)
The stereochemistry of the title reaction in several solvents has been established by 2H NMR configurational analysis of the 2-adamantyl-4,4-d2 products obtained from the α,α-dideuterated reactant 6.Solvent nucleophilic attack occurs predominantly on the side of the 2-adamantyl position away from the initial reaction site, the stereoselectivity increasing with increasing solvent nucleophilicity.Tosylate ion return in each case studied exhibits mainly though less selectively the same stereochemistry, i.e., is predominantly a non-least-motion process.Solvolysis in 80percent aqueous ethanol in the presence of 0.06 M NaN3 produces only 1percent of 2-adamantyl azide.The results constitute strong evidence for reaction through bridged carbonium ions and demonstrate that the structures of the carbocations in the initial ion pairs along the direct route and the ? route to 2-adamantyl solvolysis products are markedly differentiated by the location of the counterion.
ELECTROPHILIC ATTACK OF ELEMENTAL FLUORINE ON ORGANIC HALOGENS. SYNTHESIS OF FLUOROADAMANTANES
Rozen, Shlomo,Brand, Michael
, p. 733 - 736 (2007/10/02)
Elemental fluorine acts on bromo- and iodoadamantanes in an electrophilic mode to produce the corresponding fluoroadamantanes.The course of the reaction was investigated in several solvents.It was found that the best yields of the fluoroadamantanes were obtained when Freon (CFCl3) or Freon-chloroform was used.Using methylene chloride as a solvent with iodoadamantanes-but not with the bromo derivatives-resulted in considerable amounts of the corresponding chloro compounds.
