Studies directed towards the synthesis of trifluoromethane sulfonyl derivatives
Abstract
The syntheses of a variety of trifluoromethane sulfonyl derivatives are described. A general route for the synthesis of methyl triflone derivatives utilizing triflic anhydride is reported. Stereoselective synthesis of E-vinyl and dienyl triflones has been accomplished by the Peterson olefination reaction of a-silyl triflone anion 2.10-Li. Synthesis of $\gamma$-iodo triflones and $\gamma$-iodoallyl triflones is accomplished by regioselective addition of iodomethyl triflone to substituted alkenes and alkynes under free radical reaction conditions. The utility of this methodology is demonstrated by base elimination/oxidation of the $\gamma$-iodo triflones to afford cyclopropyl/allyl triflones. An improved method for the preparation of alkynyl triflones is described. Stereoselective synthesis of $\beta$-iodo vinyltriflones and a-stannylated vinyl triflones has been achieved. The success of palladium (0) -catalyzed synthesis of dienyl triflone 4.5 and 4.10 from iodide 4.4 and 4.9 respectively, suggests stereospecific access to a spate of trisubstituted vinyl triflones of type 4.5 and 4.10.
Degree
Ph.D.
Advisors
Fuchs, Purdue University.
Subject Area
Organic chemistry
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