Further studies on the pyrolytic domino cyclization of stabilized phosphonium ylides bearing an ortho-aminophenyl group

R. Alan Aitken; Lorna Murray; Alexandra M. Z. Slawin

doi:10.3390/molecules23092153

Further studies on the pyrolytic domino cyclization of stabilized phosphonium ylides bearing an ortho-aminophenyl group

R. Alan Aitken, Lorna Murray, Alexandra M. Z. Slawin

Research output: Contribution to journal › Article › peer-review

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 radical to afford new heterocyclic products resulting from domino cyclization of both C- and N-centred 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.

Original language	English
Article number	2153
Number of pages	12
Journal	Molecules
Volume	23
Issue number	9
DOIs	https://doi.org/10.3390/molecules23092153
Publication status	Published - 27 Aug 2018

Keywords

Phosphonium ylides
Pyrolysis
Quinoline
Phenanthridine
Benzocarbazole
X-ray structure

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© 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
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Cite this

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title = "Further studies on the pyrolytic domino cyclization of stabilized phosphonium ylides bearing an ortho-aminophenyl group",

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 radical to afford new heterocyclic products resulting from domino cyclization of both C- and N-centred 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.",

keywords = "Phosphonium ylides, Pyrolysis, Quinoline, Phenanthridine, Benzocarbazole, X-ray structure",

author = "Aitken, {R. Alan} and Lorna Murray and Slawin, {Alexandra M. Z.}",

note = "The authors thank the EPSRC (UK) for a DTA studentship (Grant No. EP/P501768/1).",

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day = "27",

doi = "10.3390/molecules23092153",

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TY - JOUR

T1 - Further studies on the pyrolytic domino cyclization of stabilized phosphonium ylides bearing an ortho-aminophenyl group

AU - Aitken, R. Alan

AU - Murray, Lorna

AU - Slawin, Alexandra M. Z.

N1 - The authors thank the EPSRC (UK) for a DTA studentship (Grant No. EP/P501768/1).

PY - 2018/8/27

Y1 - 2018/8/27

N2 - 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 radical to afford new heterocyclic products resulting from domino cyclization of both C- and N-centred 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.

AB - 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 radical to afford new heterocyclic products resulting from domino cyclization of both C- and N-centred 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.

KW - Phosphonium ylides

KW - Pyrolysis

KW - Quinoline

KW - Phenanthridine

KW - Benzocarbazole

KW - X-ray structure

UR - http://www.mdpi.com/1420-3049/23/9/2153#supplementary

U2 - 10.3390/molecules23092153

DO - 10.3390/molecules23092153

M3 - Article

SN - 1420-3049

VL - 23

JO - Molecules

JF - Molecules

IS - 9

M1 - 2153

ER -

Further studies on the pyrolytic domino cyclization of stabilized phosphonium ylides bearing an ortho-aminophenyl group

Abstract

Keywords

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