What is Truce-Smiles rearrangement?
The Truce-Smiles rearrangement, also referred to as the Smiles rearrangement, is a chemical reaction that involves an intramolecular nucleophilic aromatic substitution. This process occurs in an alkaline solution and leads to the movement of an aromatic system from one heteroatom to another within the same molecule. The connection between X and Y is typically a two-carbon unit that is frequently part of an aromatic ring. However, it can also be aliphatic in nature.
References
- A. A. Levi; , “CCCCLII.—The rearrangement of hydroxy-sulphones. Part I” J. Chem. Soc. 1931, 3264
- W. J. Evans, S. Smiles, “42. A rearrangement of o-acetamido-sulphones and -sulphides” J. Chem. Soc. 1935, 181
- W. J. Evans, S. Smiles, “74. A rearrangement of carbamyl-sulphones and -sulphides” J. Chem. Soc. 1936, 329
Full Professor of Organic Chemistry at the University of Granada, with a long-standing research career in Computational Chemistry and molecular modeling and design.