Collection of Czechoslovak Chemical Communications p. 2650 - 2662 (1994)
Update date:2022-07-30
Topics:
Ficeri, Vlastimir
Kutschy, Peter
Dzurilla, Milan
Imrich, Jan
Substituted allylic alcohols (2-buten-1-ol, 1-buten-3-ol, cinnamyl alcohol and 3-methyl-2-buten-1-ol) react with acyl isothiocyanates (4-chlorobenzoyl, 2,6-difluorobenzoyl, 3-phenylpropenoyl, 2-thienocarbonyl, 3-chloro-2-thienocarbonyl and 3-chloro-2-benzothienocarbonyl isothiocyanate) with the formation of highly reactive O-substituted allyl N-acylmonothiocarbamates, which either spontaneously or by heating in boiling benzene undergo <3,3>-sigmatropic rearrangement to S-substituted allyl N-acylmonothiocarbamates.The structure of S-series with isomerized allylic group affords the unequivocal evidence of the <3,3>-sigmatropic route of studied rearrangement.Further heating of <3,3>-rearranged N-(4-chlorobenzoyl)monothiocarbamates results in the <1,3>-sigmatropic shift of monothiocarbamate group.Using arylalkyl alcohols with the allylic double bond inserted into an aromatic system the obtained O-esters either do not undergo any rearrangement (benzyl alcohol) or undergo <1,3>-sigmatropic rearrangement (2- and 3-furylmethanol and 1-(2-furyl)ethanol) to the corresponding S-esters.For explanation of this reaction the tandem of <3,3>- and <1,3>-sigmatropic rearrangements is suggested.
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