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Cited by 9 publications
(5 citation statements)
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“…35); and the above given sequence O + < Se + ≤ S + < N + is based on purely qualitative estimates 36-38 going back to the pioneering study by Meerwein 39 ), we studied proto nation of monocyclic and the corresponding benzo annelated five membered heteroaromatic systems containing one heteroatom by quantum chemical methods. 40, 41 First semiempirical calculations at the CNDO/2 level performed about 20 years ago 42 gave the energy differences for the cations formed upon protona tion of the α and β positions (∆E α β ) that agreed with the experimental data suggesting that the positional selectiv ity decreases in the following order: furan > thiophene > > pyrrole. However, the position of selenophene between thiophene and pyrrole predicted by these calculations was in contradiction with the more recent results.…”
Section: Quantum Chemical Studies Of Positional Selectivity In Reactimentioning
confidence: 83%
See 1 more Smart Citation
“…35); and the above given sequence O + < Se + ≤ S + < N + is based on purely qualitative estimates 36-38 going back to the pioneering study by Meerwein 39 ), we studied proto nation of monocyclic and the corresponding benzo annelated five membered heteroaromatic systems containing one heteroatom by quantum chemical methods. 40, 41 First semiempirical calculations at the CNDO/2 level performed about 20 years ago 42 gave the energy differences for the cations formed upon protona tion of the α and β positions (∆E α β ) that agreed with the experimental data suggesting that the positional selectiv ity decreases in the following order: furan > thiophene > > pyrrole. However, the position of selenophene between thiophene and pyrrole predicted by these calculations was in contradiction with the more recent results.…”
Section: Quantum Chemical Studies Of Positional Selectivity In Reactimentioning
confidence: 83%
“…64 Let us only note that the geometry of the neutral N iso propylpyrrole and N (tert butyl)pyrrole molecules is in dicative of the presence of steric strain. In the former, the N(1)-C(2) bond length differs substantially from the N(1)-C(5) bond length.…”
Section: Quantum Chemical Studies Of Positional Selectivity In Reactimentioning
confidence: 99%
“…[34][35][36][37][38] The reactivity of these systems has been demonstrated with the use of electrophilic reactions producing derivatives with the electrophile substituted primarily on the pyrrole ring. [37][38][39][40][41][42][43][44] Accordingly, tricyanovinylation of thienylpyrroles 2 proceeded selectively in the pyrrole ring to form the corresponding tricyanovinyl-substituted thienylpyrroles 1.…”
Section: Synthesismentioning
confidence: 99%
“…Even when both α-positions of the pyrrole ring are occupied, electrophilic substitution will preferentially occur in the β-position of the pyrrole ring rather than the α-position of the thiophene ring. 4,[37][38][39][40] The reactivity of these systems has been demonstrated with the use of electrophilic reactions producing derivatives with the electrophile substituted primarily on the pyrrole ring. [28][29][30][31][39][40][41][42][43][44][45][46] To our knowledge, there is only one previous study describing the formylation of thienylpyrroles and this study was performed through the Vilsmeier-Haack reaction on the simple 2-(2´-thienyl)pyrrole and 2-(3´-thienyl)pyrrole.…”
Section: Vilsmeier Formylationmentioning
confidence: 99%