88218-81-9Relevant academic research and scientific papers
Radical sequential processes promoted by 1,5-radical translocation reaction: Formation and [3 + 2] anulation of alkenesulfanyl radicals
Capella, Laura,Montevecchi, Pier Carlo,Navacchia, Maria Luisa
, p. 6783 - 6789 (2007/10/03)
Radical addition of 2-substituted ethanethiols 1-5 to alkyl-, dialkyl-, and phenylacetylenes affords the corresponding β-sulfanylalkenyl radicals, which can undergo 1,5-radical translocation (RT reaction) in competition with intermolecular hydrogen abstraction (HA reaction). The RT reaction is the first step of a sequential radical process leading to alkenesulfanyl radicals through an "intermolecular sulfanyl radical transaddition" from an alkene to an alkyne molecule. Alkenesulfanyl radicals can undergo a regioselective [3 + 2] anulation reaction with a CC triple bond, eventually leading to thiophene products through 5-endo cyclization of vinyl radicals onto CC double bond. The effect of the nature of ethanethiol and alkyne substituents on the RT/HA ratio has been investigated, and results will be discussed.
Peculiar Aspects of the Anodic Oxidation of Vinylic Sulfides
Guillanton, Georges Le,Simonet, Jacques
, p. 437 - 444 (2007/10/02)
In the anodic oxidation of vinylic sulfides on platinum in acetonitrile, a non-classical sulfonium ion explains satisfactorily the transfer of the thioether group leading to an aldehyde in the presence of water, or its acetal in the presence of methanol.Some other reactions depend on the structure of the substrate, particularly the dimerization into anodically inactive forms likely to decompose during the work-up, to lead in some cases to masked ketenes having the structure of a gem-disulfide.
