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Cyclic alkenenitriles: chemoselective oxonitrile cyclizations.
Fraser F Fleming1, Lee A Funk, Ramazan Altundas
1Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282-1530, USA. flemingf@duq.edu
The Journal of Organic Chemistry
|December 21, 2002
Summary
Potassium tert-butoxide enables a one-step synthesis of carbocyclic and heterocyclic alkenenitriles from omega-oxonitriles. This chemoselective cyclization overcomes acidity differences to form five- and six-membered rings.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Chemoselective reactions are crucial for efficient organic synthesis.
- Controlling reactivity between functional groups with differing acidities presents a synthetic challenge.
Purpose of the Study:
- To develop a novel method for synthesizing carbocyclic and heterocyclic alkenenitriles.
- To investigate the chemoselective cyclization of omega-oxonitriles using potassium tert-butoxide.
Main Methods:
- Employing potassium tert-butoxide as a base to initiate domino deprotonation, cyclization, and dehydration.
- Utilizing a diverse range of omega-oxonitriles as starting materials.
Main Results:
- Achieved chemoselective cyclization between nitrile anions and remote enolizable carbonyl groups.
- Successfully synthesized five- and six-membered carbocyclic and heterocyclic alkenenitriles in a single operation.
- Demonstrated the efficiency of the domino reaction despite inherent acidity differences.
Conclusions:
- Potassium tert-butoxide is an effective reagent for the chemoselective synthesis of alkenenitriles.
- The developed method provides a versatile route to valuable carbocyclic and heterocyclic compounds.
- This domino process offers an efficient transformation of omega-oxonitriles.