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- Title
Iminium-substituted 2,3-dihydroisoxazoles: synthesis from acetylenic iminium salts and nitrones, and some transformations.
- Authors
Gerster, Holger; Keim, Michael; Maas, Gerhard
- Abstract
Keywords: acetylenic iminium salts; imidazolium salts; nitrones; thermal rearrangement; [3+2] cycloaddition; 4-isoxazolines EN acetylenic iminium salts imidazolium salts nitrones thermal rearrangement [3+2] cycloaddition 4-isoxazolines 505 515 11 07/18/22 20220701 NES 220701 1 Introduction 2,3-Dihydroisoxazoles (4-isoxazolines) are partially unsaturated five-membered O,N-heterocycles, which are known for a wide range of transformations, of which their tendency toward an array of thermal rearrangements is both synthetically useful and mechanistically remarkable. 3 Conclusions Propyniminium salts with an internal or terminal CC triple bond were identified as excellent dipolarophiles for [3+2] cycloaddition reaction with two acyclic nitrone dipoles. While reaction rates of the nitrone-alkyne cycloaddition depend on various factors, it is well known that electron-withdrawing substituents at the C C triple bond can lead to a considerable rate acceleration.
- Subjects
ISOXAZOLIDINES; NITRONES; SALTS; SALT; GUMS &; resins; SILYL group
- Publication
Zeitschrift für Naturforschung B: A Journal of Chemical Sciences, 2022, Vol 77, Issue 7/8, p505
- ISSN
0932-0776
- Publication type
Article
- DOI
10.1515/znb-2022-0014