Synthesis of 2-(perfluoroalkyl)ethyl potassium sulfates based on perfluorinated Grignard reagents was written by Paterova, Jana;Skalicky, Martin;Rybackova, Marketa;Kvicalova, Magdalena;Cvacka, Josef;Kvicala, Jaroslav. And the article was included in Journal of Fluorine Chemistry in 2010.Quality Control of 1,3,2-Dioxathiolane 2,2-dioxide This article mentions the following:
The first example of nucleophilic substitution with perfluoroalkyl Grignard reagents on the sp3 carbon center is described. Thus, a series of organometals RF-MgBr, prepared from perfluorinated alkyl iodides with alkyl group = C4F9, C6F13, C8F17, C10F21 and C12F25, reacted with 1,3,2-dioxathiolane-2,2-dioxide to afford the corresponding 2-(perfluoroalkyl)ethyl magnesium sulfates, which were isolated after metathesis to the corresponding potassium salts. In the model reaction, perfluorohexylmagnesium iodide was reacted with Me triflate yielding polyfluorinated alkane. The attempts to extend the reaction to 1,3,2-dioxathiane-2,2-dioxide were unsuccessful due to its inferior reactivity and only reduced polyfluoroalkane and the product of coupling were detected in the reaction mixture Polyfluorinated sulfates are easily hydrolyzed with hydrochloric or triflic acid to the corresponding alcs., which is an alternative to standard transformation of perfluoroalkyl iodides to 2-(perfluoroalkyl)ethanols. Quantum-chem. calculations of the PES of the reaction with both sulfur-containing heterocycles found that the failure of the reaction with 1,3,2-dioxathiane-2,2-dioxide is caused by higher activation energy of the process. In the experiment, the researchers used many compounds, for example, 1,3,2-Dioxathiolane 2,2-dioxide (cas: 1072-53-3Quality Control of 1,3,2-Dioxathiolane 2,2-dioxide).
1,3,2-Dioxathiolane 2,2-dioxide (cas: 1072-53-3) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Quality Control of 1,3,2-Dioxathiolane 2,2-dioxide
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem