Abstract
Reactions of pyrrole, imidazole, pyrazole, and 1,2,4-triazole with allene and propyne in the gas phase with formation of the corresponding N-isopropenylazoles were simulated at the RHF/6-31G**, B3LYP/6-31G**, and MP2(full)/6-31G** levels. Dissociation of the N-H bond to give azolate ion is the main constituent of the reaction coordinate. All the examined azoles react preferentially with allene rather than with propyne; their reactivity decreases in the series pyrrole > imidazole > pyrazole > 1,2,4-triazole due to participation of the pyridine type nitrogen atoms in the prototropic propyne-allene rearrangement.
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Original Russian Text © V.A. Shagun, O.A. Tarasova, B.A. Trofimov, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 7, pp. 1057–1062.
For communication II, see [1].
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Shagun, V.A., Tarasova, O.A. & Trofimov, B.A. N-isopropenylazoles: III. Quantum-chemical analysis of the reaction of azoles with allene and propyne in the gas phase. Russ J Org Chem 42, 1039–1044 (2006). https://doi.org/10.1134/S1070428006070190
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DOI: https://doi.org/10.1134/S1070428006070190