CHED Irvin Levy, Carmen Gauthier, Nicole Snyder  Sunday, April 07, 2013 

139 - Rearrangement reactions of epoxides derived from (R)-pulegone in an advanced organic laboratory

Larry G. French,, Department of Chemistry, St. Lawrence University, Canton, NY 13617, United States

Diastereoisomeric epoxides are prepared from (R)-pulegone, isolated from pennyroyal earlier in the course, via reaction with hydrogen peroxide under basic conditions. Students then explore two rearrangement reactions of these epoxides; one catalyzed by a protic acid and the other by a Lewis acid, and determine the major product(s) from each reaction. The p-toluene sulfonic acid mediated process affords predominately 2-hydroxy-5-methyl-2-(1-methylethenyl)-cyclohexanone as a mixture of two diastereoisomers. Treatment with boron triflouride etherate affords a single product, (5R)-2,2,5-trimethyl-1,3-cycloheptadione, in high yield.

Sunday, April 7, 2013 07:00 PM
General Posters (07:00 PM - 09:00 PM)
Location: Morial Convention Center
Room: Hall E2&E3


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