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A truce on the Smiles rearrangement: revisiting an old reaction—the Truce–Smiles rearrangement

2008; Royal Society of Chemistry; Volume: 37; Issue: 11 Linguagem: Inglês

10.1039/b808960d

1460-4744

Timothy J. Snape,

Innovative Microfluidic and Catalytic Techniques Innovation

The Smiles rearrangement is the intramolecular nucleophilic aromatic substitution reaction incorporating a heteroatom as the nucleophilic component and an activated electrophilic arene. One particular variation—the Truce–Smiles rearrangement—utilises a carbon-based nucleophile and an electrophilic arene which does not require additional activation. Such a variation generates a new carbon–carbon bond and the synthetic utility of this relatively under-utilised rearrangement is discussed in this tutorial review.