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Molecules 2018, 23(9), 2153; https://doi.org/10.3390/molecules23092153

Further Studies on the Pyrolytic Domino Cyclization of Stabilized Phosphonium Ylides Bearing an Ortho-Aminophenyl Group

EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK
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Received: 27 July 2018 / Revised: 14 August 2018 / Accepted: 24 August 2018 / Published: 27 August 2018
(This article belongs to the Special Issue Recent Advances in Nitrogen-Containing Aromatic Heterocycles)
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Abstract

Four new, stabilized phosphonium ylides containing a 2-(benzyl(methyl)amino)phenyl group have been prepared and characterized and are found, upon pyrolysis under gas-phase flow conditions, to lose Ph3PO and benzyl radicals to afford new heterocyclic products resulting from domino cyclization of both C- and N-centered radicals. Most products arise from processes of the former type and have quinoline, phenanthridine, or ring-fused phenanthridine structures, while in one case, a process of the latter type leads to a benzocarbazole product. The X-ray structure of a 2-(methyl(tosyl)amino)phenyl ylide is also reported. View Full-Text
Keywords: phosphonium ylide; pyrolysis; quinoline; phenanthridine; benzocarbazole; X-ray structure phosphonium ylide; pyrolysis; quinoline; phenanthridine; benzocarbazole; X-ray structure
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Aitken, R.A.; Murray, L.; Slawin, A.M.Z. Further Studies on the Pyrolytic Domino Cyclization of Stabilized Phosphonium Ylides Bearing an Ortho-Aminophenyl Group. Molecules 2018, 23, 2153.

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