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  • 1
    Electronic Resource
    Electronic Resource
    Syntheses of Cyclic and Acyclic Bis(perfluoroalkylthio)nitronium Salts (1995)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 128 (1995), S. 429-433 
    Details
    ISSN: 0009-2940
    Keywords: Nitronium ions ; One-electron oxidation ; Superacidic systems ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (F3CS)3N (1) is oxidized quantitatively by AsF5 to the first bis(perfluoroalkylthio)nitronium salt (F3CS)2N+AsF-6 (2). Addition of halide ions (F-, Cl-, Br-, l-) to the cation of 2 destroys the S—N—S chain. (F2CSCl)2 undergoes with ammonia a cyclization reaction to S—CF2—CF2—S—N—H (3), which can be derivatized with F3CSCl or (F2CSCl)2 to S—CF2—CF2—S—N—SCF3 (3a) and (S—CF2—CF2—S—N—SCF2—)2 (3b), respectively. Oxidation of 3a with AsF5 yields (S—CF2—CF2—S—N+AsF-6 (4) and byproducts, which suggest formation of a {3a}+• radical cation as an intermediate in this reaction. Pure 4 is accessible by reaction of 3 with AsF5 in 54% yield. The chemical and spectroscopic properties of the new species are discussed.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19951280416
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesen und Reaktionen acyclischer fluororganischer Thiocarbenium-IonenHerrn Prof. Dr. W. Sawodny zum 60. Geburtstag gewidmet. (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 597-603 
    Details
    ISSN: 0009-2940
    Keywords: (Trifluoromethylthio)carbon ; Carbenium ions ; One-electron oxidation ; Superacidic systems ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Syntheses and Reactions of Fluoroorganic Acyclic Thiocarbenium IonsHerrn Prof. Dr. W. Sawodny zum 60. Geburtstag gewidmet.Arsenic pentafluoride oxidizes (F3CS)4C (1) but not (F3CS)2C = C(SCF3)2 (2) to yield the stable salt (F3CS)3C+AsF-6 (3). It reacts with halide ions to form (F3CS)3CX (3a-c, X = F, Cl, Br). Iodide is oxidized to iodine with formation of (F3CS)3CC(SCF3)3 (4) which reacts with nitrogen dioxide to give (F3CS)3CNO2 (3e). - (F3CS)3C+AsF-6 (3) removes from (F)-SCF3 (5a) a ring-bound fluorine atom to afford (F3CS)3CF and -SCF3]+AsF-6 (5). When (F3CS)3CCl (3b) is treated with AsF5, 3 and [(F3CS)2-CCl]+AsF-6 (6) are formed in a 2:1 molar ratio. The latter reacts with F- or Cl- to give (F3CS)2CClX (6a,b; X = F, Cl). AsF5 is capable of abstracting a fluoride ion from (F3CS)3 - n Cln,CF only if n = 0 or 1. For n = 2 no similar reaction takes place, but with AlCl3 in BCl3 halogen exchange to F3CSCCl3 (7b) is observed. - Alkylation of (F3CS)2C=S (8) with H3CF/AsF5 yields [(F3CS)2CSCH3]+AsF-6 (9), which adds a fluoride ion to give (F3CS)2(H3CS)CF (9a). The molecular structures of (F3CS)2C = C(SCF3)2 (2) and (F3CS)3CC(SCF3)3 (4) have been determined by X-ray diffraction methods.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270403
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