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Some chlorine fluorosulfonate and peroxydisulfuryl-difluoride reactions
Authors:AV Fokin
Institution:Academy of Sciences of the USSR, Moscow, USSR
Abstract:Chlorine fluorosulfonate adds exceptionally easy not only to various alkenes, perfluorobenzene, but to alkynes too
The addition of peroxydisulfuryldifluoride to alkyl- and perfluoroalkyliodides leads to unstable adducts, which decompose with the formation of alkylfluorosulfonates and iodine fluorosulfonate; the latter was trapped with fluoroalkenes
The use of ClOSO2F allows to substitute selectively for the fluorosulfonate group the chlorine atom in monochloroacetic acid esters as well as the fluorine atom in hexafluoroacetone N-fluoroimine
ClOSO2F serves as an exceptionally active chlorinating reagent for fluorinated alcohols, nitrosocompounds, perfluoroacid amides and particularly for benzene
The reaction of (OSO2F)2 with perfluoroacid amides leads to the corresponding N,N-bis(fluorosulfonate)amides, which easily rearrange into alkylfluorosulfonates
The hypochlorites of fluorinated alcohols are stable enough and they, similarly to ClOSO2F, are able to add to alkenes, fluoroalkenes (but not to perfluoroisobutylene), bis(trifluoromethyl)ketene, trifluoromethylisocyanate and perfluoronitriles
The fluorosulfonatoacetic acid esters are unstable at the ambient temperature, but they can be widely used in situ as a very effective alkylating reagents
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