GAS-PHASE ELIMINATION-REACTIONS OF 4-SUBSTITUTED-2-ALKOXYTHIAZOLINE-5-ONES

Gas-phase eliminations of 4-substituted-2-alkoxythiazoline-5-ones have been studied. These compounds eliminate via a six-membered transition state to produce 4-substituted-thiazolidine-2,5-diones. These elimina tions are unimolecular first-order reactions. Utilization of this ther molysis reaction in the synthesis of new 4-substituted-thiazolidine-2, 5-diones is considered. Additional mechanistic information was obtaine d by comparing the kinetic data for thermal elimination reactions of t hese compounds with that of 1-ethoxythiazole. (C) 1996 John Wiley & So ns, Inc.