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1,3‐Butadienyl‐thiocyanate in der Diels ‐ Alder ‐Reaktion mit anschliessender [3,3]‐sigmatroper Umlagerung
Author(s) -
Huber Stefan,
Stamouli Peristera,
Jenny Titus,
Neier Reinhard
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690817
Subject(s) - chemistry , isothiocyanate , thiocyanate , diels–alder reaction , thiocarbamates , tropone , medicinal chemistry , sequence (biology) , organic chemistry , catalysis , biochemistry
1,3‐Butadienyl Thiocyanates in the Diels ‐ Alder Reaction Followed by a [3,3]‐Sigmatropic Shift ( 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.