A greener method of forming carbon-carbon double bonds

CHED 337

Timothy J Barker, barkert@stolaf.edu and Gary O. Spessard, spessard@stolaf.edu. Department of Chemistry, St. Olaf College, 1500 St. Olaf Avenue, Northfield, MN 55057
We present two ring-closing metathesis reactions using Grubbs first generation catalyst and a new solvent, polyethylene glycol (PEG), obtaining 100% conversion of the substrates, diethyl diallylmalonate and diallyltosylamine, to their respective products. PEG has shown itself to be a very inexpensive, effective, recyclable, and hazardless solvent, making these reactions feasible options for incorporation into introductory organic chemistry laboratory classes.