σ- versus π-Activation of Alkynyl Benzoates Using B(C6F5)3
AbstractWe have prepared a range of alkynyl benzoates in high yields and have investigated their reactivities with the strong Lewis acid B(C6F5)3. In such molecules both σ-activation of the carbonyl and π-activation of the alkyne are possible. In contrast to the reactivity of propargyl esters with B(C6F5)3 which proceed via 1,2-addition of the ester and B(C6F5)3 across the alkyne, the inclusion of an additional CH2 spacer switches off the intramolecular cyclization and selective σ-activation of the carbonyl group is observed through adduct formation. This change in reactivity appears due to the instability of the species which would be formed through B(C6F5)3 activation of the alkyne. View Full-Text
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Bähr, A.; Wilkins, L.C.; Ollegott, K.; Kariuki, B.M.; Melen, R.L. σ- versus π-Activation of Alkynyl Benzoates Using B(C6F5)3. Molecules 2015, 20, 4530-4547.
Bähr A, Wilkins LC, Ollegott K, Kariuki BM, Melen RL. σ- versus π-Activation of Alkynyl Benzoates Using B(C6F5)3. Molecules. 2015; 20(3):4530-4547.Chicago/Turabian Style
Bähr, Alexander; Wilkins, Lewis C.; Ollegott, Kevin; Kariuki, Benson M.; Melen, Rebecca L. 2015. "σ- versus π-Activation of Alkynyl Benzoates Using B(C6F5)3." Molecules 20, no. 3: 4530-4547.