New Di-, Tri-, and Tetra-Core-Functionalized Naphthalene Diimides from Reactions of Allyl Ethers with Lewis Acids

Tachapermpon, Y; Maniam, S; Wanichacheva, N; Langford, SJ

New Di-, Tri-, and Tetra-Core-Functionalized Naphthalene Diimides from Reactions of Allyl Ethers with Lewis Acids

Tachapermpon, Y Maniam, S Wanichacheva, N Langford, SJ

Permalink

Publisher:: WILEY-V C H VERLAG GMBH
Publication Type:: Journal Article
Citation:: Asian Journal of Organic Chemistry, 2017, 6, (1), pp. 47-53
Issue Date:: 2017-01-01

Closed Access

	Filename	Description	Size
	Asian J Org Chem - 2016 - Tachapermpon - New Di‐ Tri‐ and Tetra‐Core‐Functionalized Naphthalene Diimides from Reactions.pdf	Published version	1.15 MB	Adobe PDF	View/Open

Copyright Clearance Process

Recently Added
In Progress
Closed Access

This item is closed access and not available.

Full metadata record

Field	Value	Language
dc.contributor.author	Tachapermpon, Y
dc.contributor.author	Maniam, S
dc.contributor.author	Wanichacheva, N
dc.contributor.author	Langford, SJ
dc.date.accessioned	2022-10-28T06:57:21Z
dc.date.available	2022-10-28T06:57:21Z
dc.date.issued	2017-01-01
dc.identifier.citation	Asian Journal of Organic Chemistry, 2017, 6, (1), pp. 47-53
dc.identifier.issn	2193-5807
dc.identifier.issn	2193-5815
dc.identifier.uri	http://hdl.handle.net/10453/162831
dc.description.abstract	Core-substituted NDIs bearing aryl allyl ethers have a predisposition to deallylation in the presence of Lewis Acids (LA). However, under certain conditions, with appropriate choice of LA, the reaction can be controlled to yield unexpected and highly functionalized dinaphthol systems through a [3,3]-sigmatropic (Claisen) rearrangement. The major products of the rearrangement study have been characterized by X-ray crystallographic analysis and the per-substituted products are shown to undergo ring-closing metathesis to form heterocyclic core-extended NDIs. This study highlights a simple method to construct a series of important donor–acceptor building blocks for the preparation of new conjugated materials.
dc.language	English
dc.publisher	WILEY-V C H VERLAG GMBH
dc.relation	http://purl.org/au-research/grants/arc/DP130101861
dc.relation.ispartof	Asian Journal of Organic Chemistry
dc.relation.isbasedon	10.1002/ajoc.201600428
dc.rights	info:eu-repo/semantics/closedAccess
dc.subject	0305 Organic Chemistry
dc.title	New Di-, Tri-, and Tetra-Core-Functionalized Naphthalene Diimides from Reactions of Allyl Ethers with Lewis Acids
dc.type	Journal Article
utslib.citation.volume	6
utslib.for	0305 Organic Chemistry
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	closed_access	*
dc.date.updated	2022-10-28T06:57:19Z
pubs.issue	1
pubs.publication-status	Published
pubs.volume	6
utslib.citation.issue	1

Abstract:

Core-substituted NDIs bearing aryl allyl ethers have a predisposition to deallylation in the presence of Lewis Acids (LA). However, under certain conditions, with appropriate choice of LA, the reaction can be controlled to yield unexpected and highly functionalized dinaphthol systems through a [3,3]-sigmatropic (Claisen) rearrangement. The major products of the rearrangement study have been characterized by X-ray crystallographic analysis and the per-substituted products are shown to undergo ring-closing metathesis to form heterocyclic core-extended NDIs. This study highlights a simple method to construct a series of important donor–acceptor building blocks for the preparation of new conjugated materials.

Please use this identifier to cite or link to this item:

http://hdl.handle.net/10453/162831