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Microwave-accelerated Claisen rearrangements of allyl tetronates and tetramates
Authors:Rainer Schobert  Gary J. Gordon  Gillian Mullen  Ralf Stehle
Affiliation:Organisch-chemisches Laboratorium der Universität, 95440 Bayreuth, Germany
Abstract:[3,3]-Sigmatropic rearrangements of allyl tetronates and allyl tetramates to give 3-allyltetronic or -tetramic acids, respectively, proceed within 20-60 min under microwave irradiation (300 W, 130-190 °C). Consecutive (homo)sigmatropic [1,5] H-shifts such as oxa-ene reactions are promoted less effectively, which allows the isolation of Claisen intermediates of sigmatropic domino sequences, in contrast to conventional heating.
Keywords:Tetronic acid   Claisen rearrangement   Microwave   Tetramates
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