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A novel free-radical ring contraction of a cyclic carbamate
Alfred L Williams1, Teresa Abad Grillo, Daniel L Comins
1Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
The Journal of Organic Chemistry
|March 16, 2002
Abstract:
During a study on iodocyclocarbamation reactions of 2-styryl-4-piperidones, a novel ring contraction was observed. Iodocyclocarbamation of 2-styryl-4-piperidone 3 gave the bicyclic carbamate 4. Reduction of 4 under free-radical conditions effected a stereoselective ring contraction to provide oxazolidinone 6. A three-electron-three-center mechanism is proposed.