67985-39-1Relevant academic research and scientific papers
ALKYLIERUNGS- AND ARYLIERUNGSREAKTIONEN MIT GEMINALEN DITHIOLATEN
Rudorf, W. D.,Augustin, M.
, p. 329 - 336 (2007/10/02)
Acyl acetonitriles 1 react with carbon disulfide in the presence of sodium hydride to give disodium salts 2.Treatment of 2 with an alkylation reagent yields the open chain or cyclic acyl cyanketene S,S-acetals 3,4,8 and 10, respectively.Arylation to 11 is successful with 2,4-dinitro-chlorobenzene.Adding only one equivalent of methyl iodide to 2 and acidifying the reaction mixture lead to the monoalkylated compounds 7, whereas β-hydroxythioanilides 12 are available by reaction of 1 with phenyl isothiocyanate.A comparison of the ?-values shows that there exists the same type of the proton's chelation of the OH-group in 7 and 12.
