Cation radicals of organosulphur compounds

References

• Asmus K.-D. Pulse radiolysis methodology. Methods in Enzymology, L. Packer. Academic, Orlando 1984; Vol. 105: 167–178
   Google Scholar
• Baciocchi E., Fasella E., Lanzalunga O., Mattioli M. Stereochemistry of the C-S bond cleavage in 1-phenylethyl phenylsulphide radical cation: evidence for a unimolecular pathway. Angewandte Chemie International Edition in English 1993; 32: 1071–1073
   Web of Science ®Google Scholar
• Baciocchi E., Intini D., Piermattei A., Rol C., Ruzziconi R. Product and kinetic study of the oxidation of thioethers by cerium (IV) ammonium nitrate in acetic acid. Gazzetta Chimica Italiana 1989; 119: 649–652
   Google Scholar
• Bobrowski K., Schöneich C. Hydroxyl radical adduct at sulfur in substituted organic sulfides stabilized by internal hydrogen bond. Journal of the Chemical Society, Chemical Communications 1993; 795–797
   Google Scholar
• Bobrowski K., Schöneich C., Holcman J., Asmus K.-D. OH Radical induced decarboxylation of methionine containing peptides. Influence of peptide sequence and net charge. Journal of Chemical Society, Perkin Transactions 1991a; 2: 353–362
   Google Scholar
• Bobrowski K., Schöneich C., Holcman J., Asmus K.-D. OH Radical induced decarboxylation of γ-glutamylmethionine and S-alkylglutathione derivatives: evidence for two different pathways involving C- and N-terminal decarboxylation. Journal of the Chemical Society, Perkin Transactions 1991b; 2: 975–980
   Google Scholar
• Boduszek B., Shine H. J. Preparation of solid thianthrene cation radical tetrafluoroborate. Journal of Organic Chemistry 1988; 53: 5142–5143
   Google Scholar
• Ci X., Whitten D. G. Photofragmentation via single electron transfer: selective labilization of C-C bonds in amino alcohols with several bonds between heteroatom substituents. Journal of the American Chemical Society 1989; 111: 3459–3461
   Google Scholar
• Cohen S. G., Ojanpera S. Photooxidation of methionine and related compounds. Journal of the American Chemical Society 1975; 97: 5633–5634
   PubMedGoogle Scholar
• Coleman B. R., Glass R. S., Setzer W. N., Prabhu U. D. G., Wilson G. S. Electrochemistry of aliphatic thioethers as models for biological electron transfer. Advances of Chemistry Series 1982; 201: 417–441
   Google Scholar
• Davidson R. S., Pratt J. E. The titanium dioxide sensitized photo-oxidation of sulphides. Tetrahedron Letters 1983; 24: 5903–5906
   Google Scholar
• Dinnocenzo J. P., Banach T. E. Dioxygenyl hexafluoroantimonate: a useful reagent for preparing cation radical salts in good yield. Journal of the American Chemical Society 1986; 108: 6063–6065
   PubMedGoogle Scholar
• Doerge D. R. Oxygenation of organosulphur compounds by peroxidases: evidence of an electron transfer mechanism for lactoperoxidase. Archives of Biochemistry and Biophysics 1986; 244: 678–685
   PubMed Web of Science ®Google Scholar
• Drewello T., Lebrilla C. B., Asmus K.-D., Schwarz H. Dithiadications from cyclic and acyclic precursors by gas phase oxidation (charge stripping) of 3e/2c radical cations. Angewandte Chemie International Edition in English 1989; 28: 1275–1276
   Web of Science ®Google Scholar
• Engel P. S., Robertson D. M., Scholz J. N., Shine H. J. Reaction of azoalkanes with isolable cation radical salts. Journal of Organic Chemistry 1992; 57: 6178–6187
   Google Scholar
• Ekern S., Illies A., Peschke M. A novel mechanism for reactions of thiirane with the thiirane radical cation. An experimental and ab initio study. Journal of the American Chemical Society 1993; 115: 12510–12518
   Google Scholar
• Epling G. A., Wang Q. Photosensitized cleavage of the dithioprotecting group by visible light. Tetrahedron Letters 1992; 33: 5909–5912
   Google Scholar
• Fish R. H., Kimmel E. C., Casida J. E. Bioorganotin chemistry: biological oxidation of organotin compounds. Advances in Chemistry Series 1976; 157: 197–203
   Google Scholar
• Garcia H., Iborra S., Miranda M. A., Primo J. 2,4,6-Triphenyl-pyrylium tetrafluoroborate sensitized photolysis as a novel method for the hydrolytic cleavage of acetals and thioacetals. New Journal of Chemistry 1989; 13: 805–806
   Google Scholar
• Gilbert B. C., Hodgeman D. K. C., Norman R. O. C. Electron spin resonance studies part XXXVIII. Evidence for the formation of dimeric radical cations R2SSR2 in the one-electron oxidation of sulphides. Journal of the Chemical Society, Perkin Transactions 1973; 2: 1748–1752
   Google Scholar
• Gill P. M. W., Radom L. Structures and stabilities of singly charged three-electron hemibonded systems and their hydrogen-bonded isomers. Journal of the American Chemical Society 1988; 111: 4931–4941
   Google Scholar
• Glass R. S., Andruski S. W., Broker J. L. Geometric effects in sulphur lone pair interactions. Reviews on Heteroatom Chemistry, S. Oae. MYU, Tokyo 1988; 31–45
   Google Scholar
• Glass R. S., Britt W. J., Wilson G. S. 2,3,7,8-tetramethoxythianthrene dication. An isolable thianthrene dication. Journal of the American Chemical Society 1971; 95: 2375–2376
   Google Scholar
• Glass R. S., Broeker J. L., Anklam E., Asmus K.-D. Formation of sulphur-centered cation radicals by photofragmentation. Tetrahedron Letters 1992a; 33: 1721–1724
   Google Scholar
• Glass R. S., Hojjatie M., Wilson G. S., Mahling S., Göbl M., Asmus K.-D. Pulse radiolysis generation of sulphur radical cations stabilized by neighboring carboxylate and alcohol groups. Journal of the American Chemical Society 1984; 106: 5382–5383
   Web of Science ®Google Scholar
• Glass R. S., Jung W. Stereospecific conrotatory ring opening of a tetraaryl thiirane cation radical. Journal of the American Chemical Society 1994; 116: 1137–1138
   Google Scholar
• Glass R. S., Petsom A., Wilson G. S., Martinez R., Juaristi E. Electrosynthesis of substituted 1,2-dithiolane-1-oxides from substituted 1,3-dithianes. Journal of Organic Chemistry 1986; 51: 4337–4342
   Web of Science ®Google Scholar
• Glass R. S., Radspinner A. M., Singh W. P. Neighboring tin effect in electron transfer from thioethers. Journal of the American Chemical Society 1992b; 114: 4921–4923
   Google Scholar
• Goslich R., Weiss J., Möckel H. J., Mönig J., Asmus K.-D. A novel rearrangement in (R2S.: SR2)+ radical cations with a 3e bond. Angewandte Chemie International Edition in English 1985; 24: 73–74
   Google Scholar
• Haag T., Lingens F., Van Pée K.-H. A metal ion and cofactor-independent enzymatic redox reaction: halogenation by bacterial nonheme haloperoxidases. Angewandte Chemie International Edition in English 1991; 30: 1487–1488
   Google Scholar
• Hammerich O., Parker V. D. Kinetics and mechanisms of reactions of organic cation radicals in solution. Advances in Physical Organic Chemistry 1984; 20: 55–189
   Web of Science ®Google Scholar
• Iranpoor N., Owji J. Regioselective alcoholysis and conversion of thiiranes to alkoxy-disulphides with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ). Synthetic Communications 1990; 20: 1047–1053
   Web of Science ®Google Scholar
• Iranpoor N., Owji J. Efficient, mild, and regioselective conversion of thiiranes to alkoxy and acetoxy disulphides and dithianes with Ce(IV) based oxidants. Tetrahedron 1991; 47: 149–154
   Web of Science ®Google Scholar
• Jones G., II, Huang B., Griffin S. F. Electron-transfer photochemistry of thianthrene. Nucleophile-assisted photooxidation to sulphoxide. Journal of Organic Chemistry 1993; 58: 2035–2042
   Google Scholar
• Kamata M., Miyashi T. The photochemical [3 + 2] cycloaddition reaction of 2,2,3,3-tetraarylthiiranes and TCNE through donor-acceptor complexes. Journal of the Chemical Society, Chemical Communications 1989a; 557–558
   Google Scholar
• Kamata M., Murayama K., Miyashi T. Aminium radical salt catalyzed desulphurization of thiiranes: an efficient preparation of aryl substituted olefins. Tetrahedron Letters 1989b; 30: 4129–4132
   Web of Science ®Google Scholar
• Kamata M., Murayama K., Suzuki T., Miyashi T. A novel reaction of thiirane cation radicals in solutions: the formation of 5,6-diphenyl-1,2,3,4-tetrathianes through trisulphurated thiirane cation radical intermediates. Journal of the Chemical Society, Chemical Communications 1990; 827–829
   Google Scholar
• Kobayashi S., Nakano M., Kimura T., Schaap A. P. On the mechanism of the peroxidase-catalyzed oxygen-transfer reaction. Biochemistry 1987; 26: 5019–5022
   PubMed Web of Science ®Google Scholar
• Krusic P. J., Kochi J. K. Conformational effects of sulfur, silicon, germanium, and tin on alkyl radicals. An electron spin resonance study of the barriers to internal rotation. Journal of the American Chemical Society 1971; 93: 846–859
   Google Scholar
• Lochynski S., Boduszek B., Shine H. J. Oxidation of organotins (R4Sn, RSnMe3, and R3SnSnR3) by the thianthrene cation radical. Journal of Organic Chemistry 1991; 56: 914–920
   Google Scholar
• Lyons A. R., Symons M. C. R. Electron spin resonance evidence for greatly enhanced hyperconjugation in radicals containing tin, phosphorus, and arsenic. Journal of the Chemical Society, Chemical Communications 1971; 1068–1069
   Google Scholar
• Mahling S., Asmus K.-D., Glass R. S., Hojjatie M., Wilson G. S. Neighboring group participation in radicals: pulse radiolysis studies on radicals with sulphur-oxygen interaction. Journal of Organic Chemistry 1987; 52: 3717–3724
   Google Scholar
• Mallet J.-M., Meyer G., Yvelin F., Jutand A., Amatore C., Sinaÿ P. Electrosynthesis of disaccharides from phenyl or ethyl 1-thioglycosides. Carbohydrate Research 1993; 244: 237–246
   PubMed Web of Science ®Google Scholar
• Mao Y., Thomas J. K. Photoinduced electron transfer and subsequent chemical reactions of absorbed thianthrene on clay surfaces. Journal of Organic Chemistry 1993; 58: 6641–6649
   Google Scholar
• Miller A. E., Bischoff J. J., Bizub C., Luminoso P., Smiley S. Electronic and steric effects in oxidations by isoalloxazine 4a-hydroperoxides. Journal of the American Chemical Society 1986; 108: 7773–7778
   PubMedGoogle Scholar
• Mitchell S. C., Nickson R. M. Metabolism of sulphur-containing xenobiotics. Sulphur Reports 1993; 13: 161–195
   Google Scholar
• Musker W. K., Wolford T. L., Roush P. B. An investigation of mesocyclic and acyclic dithioether cation radicals and dications. Journal of the American Chemical Society 1978; 100: 6416–6421
   Web of Science ®Google Scholar
• Oae S., Mikami A., Matsuura T., Ogawa-Asada K., Watanabe Y., Fujimori K., Iyanagi T. Comparison of sulphide oxygenation mechanism for liver microsomal FAD-containing monooxygenase with that for cytochrome P-450. Biochemical and Biophysical Research Communications 1985; 131: 567–573
   PubMed Web of Science ®Google Scholar
• Oae S., Watanabe Y., Fujimori K. Biomimetic oxidation of organic sulphides with TPP Fe(III) Cl/imidazole/hydrogen peroxide. Tetrahedron Letters 1982; 23: 1189–1192
   Web of Science ®Google Scholar
• Pattenden G., Stapleton A., Humber D. C., Roberts S. M. Novel alkoxylations of cephalosporins by cerium(IV) salts and by electrooxidative procedures. Journal of the Chemical Society, Perkin Transactions 1988; 1: 1685–1688
   Google Scholar
• Pienta N. J. Amines, thiols, and thioethers: heteroaromatic electron donors. Photoinduced Electron Transfer part C, M. A. Fox, M. Chanon. Elsevier, Amsterdam 1988; 421–486
   Google Scholar
• Pryor W. A., Hendrickson W. H., Jr. Reaction of nucleophiles with electron acceptors by SN2 or electron transfer (ET) mechanisms: tert-butyl peroxybenzoate/dimethyl sulphide and benzoylperoxide/N,N-dimethyl aniline systems. Journal of the American Chemical Society 1983; 105: 7114–7122
   Web of Science ®Google Scholar
• Qin X.-Z., Meng Q., Williams F. ESR studies of the thietane and thiirane radical cations in freon matrices. Evidence for ethylene molecule extrusion from the * thiirane dimer radical cation [C2H4S-SC2H4+.]. Journal of the American Chemical Society 1987; 109: 6778–6788
   Google Scholar
• Riley D. P., Smith M. R., Correa P. E. Selective molecular oxygen oxidation of thioethers to sulphoxides catalyzed by Ce(IV). Journal of the American Chemical Society 1988; 110: 177–180
   Web of Science ®Google Scholar
• Ryan M. D., Swanson D. D., Glass R. S., Wilson G. S. Studies of the EE mechanism. Evidence for reversible dimer formation in electrochemical oxidation of acyclic dithioether. Journal of Physical Chemistry 1981; 85: 1069–1075
   Web of Science ®Google Scholar
• Schöneich C., Aced A., Asmus K.-D. Mechanism of oxidation of aliphatic thioethers to sulphoxides by hydroxyl radicals. The importance of molecular oxygen. Journal of the American Chemical Society 1993; 115: 11376–11383
   Web of Science ®Google Scholar
• Stfffen L. K., Glass R. S., Sabahi M., Wilson G. S., Schöneich C., Mahling S., Asmus K.-D. OH radical induced decarboxylation of amino acids. Decarboxylation vs bond formation in radical intermediates. Journal of the American Chemical Society 1991; 113: 2141–2145
   Google Scholar
• Symons M. C. R. Radical cations in condensed phases. Chemical Society Reviews 1984; 13: 393–439
   Web of Science ®Google Scholar
• Takemoto Y., Ohra T., Koike H., Furuse S., Iwata C. Chirality preservation of a cation-radical intermediate. Tandem oxidative ring expansion-cyclization reaction of optically active bicyclo[4.1.0]heptyl sulphides. Journal of Organic Chemistry 1994; 59: 4727–4729
   Google Scholar
• Venimadhavan S., Amarnath K., Harvey N. G., Cheng J.-P., Arnett E. M. Heterolysis, homolysis, and cleavage energies for the cation radicals of some carbon-sulphur bonds. Journal of the American Chemical Society 1992; 114: 221–229
   Google Scholar
• Watanabe Y., Oae S., Iyanagi T. Mechanisms of enzymatic S-oxygenation of thioanisole derivatives and O-demethylation of anisole derivatives promoted by both microsomes and a reconstituted system with purified cytochrome P-450. Bulletin of the Chemical Society of Japan 1982; 55: 188–195
   Web of Science ®Google Scholar
• Werst D. W. Radical cation complexes formed by α-lone pair interactions. Journal of Physical Chemistry 1992; 96: 3640–3646
   Google Scholar
• Wilson G. S., Swanson D. D., Klug J. T., Glass R. S., Ryan M. D., Musker W. K. Electrochemical oxidation of some mesocyclic dithioethers and related compounds. Journal of the American Chemical Society 1979; 101: 1040–1042
   Web of Science ®Google Scholar
• Yoshida J., Maekawa T., Murata T., Matsunaga S., Isoe S. The origin of the β-silicon effect in electron-transfer reactions of silicon-substituted heteroatom compounds. Electrochemical and theoretical studies. Journal of the American Chemical Society 1990; 112: 1962–1970
   Web of Science ®Google Scholar