Faculté des sciences

1,3-Butadienyl-thiocyanate in der Diels-Alder-Reaktion mit anschliessender [3,3]-sigmatroper Umlagerung = 1,3-Butadienyl Thiocyanates in the Diels-Alder Reaction Followed by a [3,3|-Sigmatropic Shift

Huber, Stefan ; Stamouli, Peristera ; Jenny, Titus ; Neier, Reinhard

In: Helvetica Chimica Acta, 1986, vol. 69, no. 8, p. 1898-1915

(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 a [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,... More

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    Summary
    (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 a [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.