The mechanism of solvolysis of 2-adamantyl azoxytosylate: isotopic labelling, medium effect, and attempted deoxygenation studies
Article Abstract:
Rates of solvolysis of 2-adamantyl azoxytosylate have been measured for a range of temperatures in 50:50 trifluoroethanol:water, 80:20 trifluoroethanol:water, 70:30 ethanol:water, 97:3 trifluoroethanol:water, in methanoic acid and in ethanoic acid. Rates of solvolysis of 2-adamantyl tosylate have been measured, for comparison, in 80:20, 90:10 and 50:50 trifluoroethanol:water. For both compounds activation parameters have been found. The m value for 2-adamantyl axosytosylate solvolysis is 0.46, very low for any reaction clearly an SN1 solvolysis. Labelling studies with isotopes have given information about the SN1 fragmentation mechanism of 2-adamantyl azoxytosylate.
Publication Name: Canadian Journal of Chemistry
Subject: Chemistry
ISSN: 0008-4042
Year: 1998
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The acid dissociation constant of triphenylethenethiol, a simple thioenol, and that of its oxygen-enol analog
Article Abstract:
The acidity constant for the stable, simple thioenol triphenylethenethiol has been evaluated through use of spectrophotometric titration and is 8.49. For its unstable oxygen-enol analog the value is 11.37. It was determined by analyzing the ketonization rate through use of enol generated from triphenylvinyl bromide with flash photolysis. Apparently this is the first time acid strength of a simple thioenol has been determined.
Publication Name: Canadian Journal of Chemistry
Subject: Chemistry
ISSN: 0008-4042
Year: 1998
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