6401-03-2Relevant academic research and scientific papers
Synthesis and Reactions of Perfluorobutanesulfonyl Hypohalites
Johri, Kamalesh, K.,DesMarteau, Darryl D.
, p. 5081 - 5086 (1981)
Two new hypohalites, perfluoro-n-butanesulfonyl hypochlorite and hypobromite, are reported.The hypochlorite is prepared by the low-temperature reaction of ClF with the acid C4F9SO2OH.The hypobromite is prepared by reaction of the hypochlorite with bromine.The new compounds contain very electrophilic halogen atoms and exhibit reactions similar to the analogous trifluoromethanesulfonates, CF3SO2OX (X=Cl, Br).The new hypohalites exhibit somewhat greater stability than the trifluoromethanesulfonates but form analogous decomposition products.Characterization of the newcompounds is given along with several reactions with olefins and halides to yield a variety of new esters.
Preparation of Esters of Nonafluorobutanesulfonic Acid
Frasch, Markus,Sundermeyer, Wolfgang,Waldi, Joachim
, p. 1763 - 1768 (2007/10/02)
A series of new alkyl (2a-e), silyl (6a-l), germyl (7) and stannyl esters (8a, b) of nonafluorobutanesulfonic acid has been prepared by different methods (A-I) e.g.C4F9SO2OR and C4F9SO2OSiR3 .These compounds are useful and extremely powerful alkylating or silylating reagents. Key Words: Nonanfluorobutanesulfonic acid, alkyl and silyl esters / Alkylation / Silylation
Alkylation of 1,3-Dithietane 1,1,3,3-Tetroxide (Disulfene) by Nonafluorobutanesulfonates
Frasch, Markus,Sundermeyer, Wolfgang,Waldi, Joachim
, p. 1805 - 1807 (2007/10/02)
Silyl and alkyl esters of nonafluorobutanesulfonic acid are extremely powerful substitution reagents for disulfenes.Starting from trans-2,4-trimethylsilyldisulfene (1) and methyl nonafluorobutanesulfonate (11), 2,4-dimethyl-2,4-bis(trimethylsilyl)-1,3-dithietane 1,1,3,3-tetroxide (2) is prepared. 2 is hydrolyzed to 2,4-dimethyl-1,3-dithietane 1,1,3,3-tetroxide (3).Rapid H/D exchange reaction of 3 with D2O leads to 4.Compound 3 is deprotonated by aqueous potassium hydroxide and a potassium salt is obtained, the structure of which is most probably 5a. 2,2,4,4-Tetramethyl-1,3-dithietane 1,1,3,3-tetroxide (7) is obtained from 5 and methyl iodide, i.e. the ring system remains intact, whereas hydrolysis furnishes the ring-opened product 6. - Three new routes for the synthesis of methyl nonafluorobutanesulfonate (11) via the silver salt of 9 or dimethyl sulfate (96percent yield) or nonafluorobutanesulfonic anhydride (10) are described. Key Words: 1,3-Dithietane 1,1,3,3-tetroxides, substituted/ Nonafluorobutanesulfonates
