Abstract
Cis-butene-2 yields with Tl(III)trifluoroacetate by cis-addition of two trifluoroacetoxygroups the bis-2,3-trifluoroacetate 1a of the mesobutane diol, whereas the trans-butene-2 affords the bis-2,3-trifluoroacetate of the racemic threo-compound as expected 2a. Cyclohexene is transformed by Tl(III)trifluoroacetate to the cyclotrimeric form 3a of cyclopentylaldehyde. Cis-cyclooctene is oxidized to trifluoroacetate 4a of cyclooctene-1-ol-3. The homoallylic alcohol 5 (cyclohexene-1-ol-4) suffers a remarkable—but not unexpected—fragmentation to Z-trifluoroacetoxy-hexene-4-al-5 5a. By treating the conjugated dienes cyclohexadiene and cyclopentadiene with this reagent only cis-addition of two trifluoroacetoxygroups takes place under formation of the mixture of cis-1,4-bis-trifluoroacetoxy-cyclohexene-2( 8a) and cis-1,2-bis-trifluoroacetoxy-cyclohexene-3( 8b) on the one and cis-1,4-bis-trifluoroacetoxy-cyclopentene-2( 9a) plus cis-1,2-bis-trifluoroacetoxy-cyclopentene-3( 9b) on the other side. 1,3-Butadiene and 2,3-dimethyl-butadiene are transformed under solely 1,2-addition of the trifluoroacetoxygroups to the bis-trifluoroacetoxy compounds 6a and 7a.
Published Version
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