Journal of Undergraduate Research
Keywords
stereo-selective photochemical, cycloaddition, radical stabilization
College
Physical and Mathematical Sciences
Department
Chemistry and Biochemistry
Abstract
Organic chemistry centers around the stereo- and regioselective formation of C–C bonds. Although [4+2] and [2+2] cycloadditions present the opportunity for single-step creation of multiple stereocenters and two C–C bonds, the products resulting from intermolecular cycloadditions can be hard to predict and yields of any single isomer can be low. These obstacles can be overcome by the use of a removable tether, which induces regio- and stereo-control through the forced intramolecular reaction. The silyl acetal-tethered [2+2] photocycloaddition has been shown to produce high yields of a single product when both of the reacting alkenes contain extended p-systems. This phenomenon is considered as being due to either p-stacking between the alkene groups or radical stabilization.
Recommended Citation
Parent, Alexander and Fleming, Dr. Steven
(2013)
"Stereo-selective Photochemical [2+2] Cycloaddition: π-π Interactions or Radical Stabilization,"
Journal of Undergraduate Research: Vol. 2013:
Iss.
1, Article 2513.
Available at:
https://scholarsarchive.byu.edu/jur/vol2013/iss1/2513