Helvetica Chimica Acta p. 1898 - 1915 (1986)
Update date:2022-08-05
Topics:
Huber, Stefan
Stamouli, Peristera
Jenny, Titus
Neier, Reinhard
(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.
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