1,3-Butadienyl-thiocyanate in der Diels-Alder-Reaktion mit anschliessender -sigmatroper Umlagerung

Article abstract of DOI:10.1002/hlca.19860690817

(E)- and (Z)-1,3-Butadienyl thiocyanates 3, 4, and 12-15 have been synthesized selectively.Their use as dienes for Diels-Alder reactions followed by <3,3>-sigmatropic shift to obtain an isomeric isothiocyanate has been studied.The butadienyl thiocyanates are, unfortunately, not very reactive in Diels-Alder reactions.This disadvantage can be overcome, if a trapping reaction with EtOH is added to the two-step sequence.This sequence allows to get good yields of the O-ethyl thiocarbamates 18-23, even if the first two reactions have not favorable equilibrium constants.