51624-52-3Relevant academic research and scientific papers
Formation and transformations of cations obtained from 1,1-dialkoxyalkanes in fluorosulfonic acid
Akhmatdinov, R. T.,Kantor, E. A.,Imashev, U. B.,Yasman, Ya. B.,Rakhmankulov, D. L.
, p. 626 - 630 (2007/10/02)
The reaction of 1,1-dialkoxyalkanes with fluorosulfonic acid at -75 deg C leads to the formation of alkoxycarbenium ions and protonated alcohols.The methoxy- and ethoxymethylcarbenium ions are stable at room temperature.Methoxycarbenium undergoes further reactions at -5 deg C.At -15 deg C ethoxycarbenium is converted by a 1,3-hydride shift into methoxymethylcarbenium.At this temperature the latter reacts with ethanol, forming ethoxymethylcarbenium and methanol.At -45 deg C isopropoxycarbenium is converted also by a 1,3-hydride shift into methoxydimethylcarbenium.Methyl, ethyl, and isopropyl alcohols are converted into the corresponding fluorosulfonic esters.
1,3-HYDRIDE SHIFT IN METHOXY-, ETHOXY-, AND PROPYLOXYMETHYL CATIONS
Akhmatdinov, R. T.,Kantor, E. A.,Karakhanov, R. A.,Rakhmankulov, D. L.
, p. 400 - 403 (2007/10/02)
When dialkoxymethanes are dissolved in fluorosulfonic acid at -70 deg.C, the alkoxycarbenium ions RCH2O=CH2(1+) and the corresponding alcohols RCH2OH are formed.If the temperature is raised to -20 deg.C a 1,3-hydride shift occurs in the ions, leading to the formation of the more stable RCH=OCH3(1+) cations.The alternative path to the formation of the latter by intermolecular hydride transfer is not realized.A degenerate 1,3-hydride shift occurs in the methoxymethyl cation at 40 deg.C.
