934478-83-8Relevant articles and documents
Selective thiylation of 1-vinylpyrrole-2-carbaldehydes: Synthesis of the novel pyrrole synthons 2-[bis(ethylsulfanyl)methyl]-1-vinylpyrroles and 1-(2-ethylthioethyl)pyrrole-2-carbaldehydes
Vasil'tsov, Alexander M.,Ivanov, Andrey V.,Ushakov, Igor A.,Mikhaleva, Al'bina I.,Trofimov, Boris A.
, p. 452 - 456 (2007/12/27)
1-Vinylpyrrole-2-carbaldehydes have been selectively thiylated with ethanethiol either at the aldehyde (acid catalysis) or at the N-vinyl group (free-radical initiation) to afford 1-vinylpyrrole-2-carbaldehyde thioacetals (88-99% yield) or 1-(2-ethylthioethyl)pyrrole-2-carbaldehydes (68-89% yield), respectively. Both derivatives constitute important new families of pyrrole building blocks. Exhaustive thiylation at both the aldehyde and vinyl functionalities was achieved by acid-catalyzed reaction of the ethylthioethyl derivative of pyrrole-2-carbaldehyde with ethane thiol. An unexpected reduction of the ethylthioacetal group by ethanethiol to give the ethylthiomethyl group under free-radical initiation was also observed and is discussed. Georg Thieme Verlag Stuttgart.
