1999
DOI: 10.1039/a809268k
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The mechanism of formation of 8,8-dimethyl[4.2.1.03,7]nonan-6-yl acetate (fortesyl acetate) during acetolysis of nopyl toluene-p-sulfonate

Abstract: Attempts to prepare 2-(2-hydroxyethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene (nopol; 1) labelled with deuterium at C-10 by a process of oxidation of the primary alcohol group of nopol to the aldehyde, followed by H/D exchange and reduction back to alcohol, were unsuccessful because various oxidation procedures, including reaction with N-chlorosuccinimide at Ϫ78 ЊC, gave instead a carboxylic acid having an oxygen at C-3. Nopol, labelled at C-11 with deuterium, was obtained through a Prins reaction of β-pinene wi… Show more

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