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Tanriver G, Dagoneau D, Karadeniz U, et al. Keteniminium Salts: Reactivity and Propensity toward Electrocyclization Reactions. J Org Chem. 2019;85(2):449-463doi: 10.1021/acs.joc.9b02466.
Tanriver, G., Dagoneau, D., Karadeniz, U., Kolleth, A., Lumbroso, A., Sulzer-Mossé, S., De Mesmaeker, A., & Catak, S. (2020). Keteniminium Salts: Reactivity and Propensity toward Electrocyclization Reactions. The Journal of organic chemistry, 85(2), 449-463. https://doi.org/10.1021/acs.joc.9b02466
Tanriver, Gamze, et al. "Keteniminium Salts: Reactivity and Propensity toward Electrocyclization Reactions." The Journal of organic chemistry vol. 85,2 (2020): 449-463. doi: https://doi.org/10.1021/acs.joc.9b02466
Tanriver G, Dagoneau D, Karadeniz U, Kolleth A, Lumbroso A, Sulzer-Mossé S, De Mesmaeker A, Catak S. Keteniminium Salts: Reactivity and Propensity toward Electrocyclization Reactions. J Org Chem. 2020 Jan 17;85(2):449-463. doi: 10.1021/acs.joc.9b02466. Epub 2019 Dec 16. PMID: 31790586.
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J Org Chem. 2020 Jan 17;85(2):449-463. doi: 10.1021/acs.joc.9b02466. Epub 2019 Dec 16.

Keteniminium Salts: Reactivity and Propensity toward Electrocyclization Reactions.

The Journal of organic chemistry

Gamze Tanriver, Dylan Dagoneau, Ulfet Karadeniz, Amandine Kolleth, Alexandre Lumbroso, Sarah Sulzer-Mossé, Alain De Mesmaeker, Saron Catak

Affiliations

  1. Department of Chemistry , Bogazici University , Bebek, 34342 Istanbul , Turkey.
  2. Crop Protection Research, Research Chemistry , Syngenta Crop Protection AG , Schaffhauserstrasse 101 , CH-4332 Stein , Switzerland.

PMID: 31790586 DOI: 10.1021/acs.joc.9b02466

Abstract

A predictive computational study was conducted in order to assess the efficiency of electrocyclization reactions of keteniminium salts, in an effort to form a variety of heterocyclic systems, namely, 3-amino(benzo)thiophenes, 3-amino(benzo)furans, 3-aminopyrroles, as well as 3-aminoindoles. A density functional theory (DFT) approach was utilized and the effect of heteroatoms (NMe, O, S) was thoroughly investigated by means of population analysis, QTAIM, NICS, ACID, and local reactivity descriptors (Parr and Fukui functions). The electrocyclization of enamines leading to 3-aminopyrroles was shown to be both kinetically and thermodynamically most favorable. Moreover, the pericyclic nature of the electrocyclizations was confirmed using FMO, QTAIM, NICS, and ACID methods. Additionally, substituent effects were investigated in order to give further insight on the reactivity of heteroatom containing keteniminium systems toward electrocyclization reactions. Finally, computational predictions were experimentally confirmed for a selection of keteniminium systems.

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