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

Yordkhuan Tachapermpon, Subashani Maniam, Nantanit Wanichacheva, Steven J. Langford

Research output: Contribution to journalArticleResearchpeer-review

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)47-53
Number of pages7
JournalAsian Journal of Organic Chemistry
Volume6
Issue number1
DOIs
Publication statusPublished - 1 Jan 2017

Keywords

  • Claisen rearrangement
  • furans
  • Lewis acids
  • naphthalene diimides
  • ring-closing metathesis

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