Intermediates in nucleophilic aromatic substitution. 20. Rate-limiting proton transfer in the formation of Meisenheimer complexes between 1,3,5-trinitrobenzene and amines. The effect of dimethyl sulfoxide on proton-transfer rates. Relative leaving-group abilities of amines and alkoxide ions

1979 ◽  
Vol 44 (18) ◽  
pp. 3189-3196 ◽  
Author(s):  
Claude F. Bernasconi ◽  
Morris C. Muller ◽  
Peter Schmid
Keyword(s):  
Proton Transfer ◽  
Dimethyl Sulfoxide ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Transfer Rates ◽  
Meisenheimer Complexes ◽  
Leaving Group ◽  
Rate Limiting

scholarly journals The Truce–Smiles rearrangement and related reactions: a review

2017 ◽  
Vol 95 (5) ◽  
pp. 483-504 ◽  
Author(s):  
Anna R.P. Henderson ◽  
Joel R. Kosowan ◽  
Tabitha E. Wood
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Future Research ◽  
Tandem Reaction ◽  
Aromatic Substitution ◽  
Smiles Rearrangement ◽  
Research Directions ◽  
Reaction Method ◽  
Design Variables ◽  
Leaving Group ◽  
Future Research Directions

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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