76500-89-5Relevant academic research and scientific papers
Solvolysis of Alkyl Azoxytosylates: The Link between Solvolytic Deamination and Tosylate Solvolysis
Conner, John K.,Maskill, Howard
, p. 342 - 348 (2007/10/02)
Products of the solvolysis of 2-adamantyl azoxytosylate in acetic acid, ethanol, aqueous ethanol, trifluoroethanol, and aqueous trifluoroethanol have been analyzed by a combination of glc and hplc.The yield of 2-adamantyl tosylate by internal ion-pair combination is 32 percent in acetic acid but decreases with the increasing ionizing power of the solvent.Solvolysis products of bicyclooctan-2-yl azoxytosylate in 97:3 hexafluoropropan-2-ol:water have also been analyzed.Both systems yield hydrocarbon and solvent derived substitution products in amounts which are much closer to those obtained from solvolysisnof the corresponding tosylates than from the corresponding solvolytic deaminations even though the rate-determing step in the solvolysis of the azoxytosylates resembles closely the deaminative fragmentation.These results allow new insights into the nature of the mechanism of deamination generally.
