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The Truce–Smiles rearrangement and related reactions: a review

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Author

Henderson, Anna R. P.
Kosowan, Joel R.
Wood, Tabitha E.

Uri

http://hdl.handle.net/10680/1777

Date

2017-01-16

Doi

10.1139/cjc-2016-0594

Citation

Henderson, Anna R. P., Joel R. Kosowan, and Tabitha E. Wood, "The Truce-Smiles rearrangement and related reactions: a review." Canadian Journal of Chemistry 95(5) (2017): 483-504. DOI: 10.1139/cjc-2016-0594.

Abstract

The Truce–Smiles rearrangement is an X → C aryl migration reaction that is achieved by an intramolecular nucleophilic aromatic substitution pathway. The reaction exhibits a wide substrate scope with respect to a migrating aryl ring and leaving group, appearing in many different tandem reaction sequences, to achieve a wide variety of product outcomes. We present an extensive survey of reported examples of the Truce–Smiles rearrangement from the chemistry literature (1950s until present) organized by various substrate design variables or aspects of the reaction method. Present deficiencies in our understanding of the reaction are identified with recommendations for future research directions and useful developments in the application of the reaction are celebrated.

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