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A novel access to 3-aryl-2-norbornyl cation
Mariella Mella1, Silvia Esposti, Maurizio Fagnoni
1Department of Organic Chemistry, University of Pavia, via Taramelli 10, 27100 Pavia, Italy.
Chemical Communications (Cambridge, England)
|April 22, 2003
Summary
Researchers discovered a new way to create the 2-norbornyl cation using light and a special cation, avoiding harsh acids. The outcome, nortricyclene or addition, depends on the solvent used.
Area of Science:
- Organic Chemistry
- Photochemistry
- Carbocation Chemistry
Background:
- The 2-norbornyl cation is a classic example in carbocation chemistry.
- Traditional methods for generating this cation often require strongly acidic conditions, limiting their applicability.
Purpose of the Study:
- To develop a novel, mild method for accessing the 2-norbornyl cation.
- To investigate the influence of reaction conditions on the fate of the generated cation.
Main Methods:
- Photochemical generation of the 4-dimethylaminophenyl cation.
- Addition reaction of the photogenerated cation to 2-norbornene under mild conditions.
Main Results:
- Successfully synthesized the 2-norbornyl cation under non-acidic, mild conditions.
- Demonstrated that the reaction outcome (deprotonation to nortricyclene or nucleophile addition) is solvent-dependent.
Conclusions:
- Photochemical generation offers a new route to the 2-norbornyl cation.
- Solvent choice is critical in controlling the reactivity and product distribution of the 2-norbornyl cation.