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Title: Synthesis of mesoionic triazolones via a formal [3+2] cycloaddition between 4-phenyl-1,2,4-triazoline-3,5-dione and alkynes
Authors: Kuroda, Yusuke  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0003-0952-7098 (unconfirmed)
Krell, Maya
Kurokawa, Kazuma
Takasu, Kiyosei  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-1798-7919 (unconfirmed)
Author's alias: 黒田, 悠介
黒川, 宗希
高須, 清誠
Issue Date: 14-Feb-2024
Publisher: Royal Society of Chemistry (RSC)
Journal title: Chemical Communications
Volume: 60
Issue: 13
Start page: 1719
End page: 1722
Abstract: 1, 2, 4-Triazoline-3, 5-diones (TADs) are versatile reagents and have found widespread adoption in chemical science. Despite their remarkable reactivity toward a wide array of unsaturated hydrocarbons, the chemical reaction between TADs and alkynes has remained largely unexplored. Herein, we demonstrate that 1, 1, 1, 3, 3, 3-hexafluoro-2-propanol facilitates the unusual [3+2] cycloaddition between 4-phenyl-1, 2, 4-triazoline-3, 5-dione and alkynes, resulting in the formation of unprecedented mesoionic triazolones. Moreover, the structural properties of the resulting triazolone have been investigated by employing X-ray diffraction analysis and Density Functional Theory (DFT) calculations.
Rights: This is an accepted manuscript of this article which has been published in final form at https://doi.org/10.1039/d3cc05088b.
The full-text file will be made open to the public on 19 Jan 2025 in accordance with publisher's 'Terms and Conditions for Self-Archiving'
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/286961
DOI(Published Version): 10.1039/d3cc05088b
PubMed ID: 38240015
Appears in Collections:Journal Articles

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