Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/90122
Title: Platinum-catalysed ring-opening isomerisation of piperidine cyclopropanes
Authors: Barát, Viktor
Kasinathan, Sivarajan
Bates, Roderick Wayland
Keywords: Cyclopropane
Isomerisation
DRNTU::Science::Chemistry
Issue Date: 2018
Source: Barát, V., Kasinathan, S., & Bates, R. W. (2018). Platinum-Catalysed Ring-Opening Isomerisation of Piperidine Cyclopropanes. Asian Journal of Organic Chemistry, 7(4), 815-818. doi:10.1002/ajoc.201700706
Series/Report no.: Asian Journal of Organic Chemistry
Abstract: A range of cyclopropyl‐fused N‐tosyl piperidines have been synthesised and shown to undergo ring‐opening isomerisation on treatment with platinum(II) catalysts. The products can have either an endo‐cyclic or exo‐cyclic double bond. The selectivity is influenced by reaction temperature, solvent and, most significantly, the catalyst. A mechanism involving C−C bond activation and β‐hydride elimination is proposed. When β‐hydride elimination is blocked, a stereospecific platinum‐driven Wagner–Meerwein shift is observed.
URI: https://hdl.handle.net/10356/90122
http://hdl.handle.net/10220/48397
ISSN: 2193-5807
DOI: 10.1002/ajoc.201700706
Rights: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version of the following article: Barát, V., Kasinathan, S., & Bates, R. W. (2018). Platinum-Catalysed Ring-Opening Isomerisation of Piperidine Cyclopropanes. Asian Journal of Organic Chemistry, 7(4), 815-818., which has been published in final form at http://dx.doi.org/10.1002/ajoc.201700706. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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