Abstract
AbstractCore‐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.
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