Fascinating Organosulfur Functionalities: Polychalcogens as Diatomic Sulfur Sources

Recent work on the chemistry of dialkoxy disulfides is summarized. It includes various aspects of their structure and relationship to the isomeric thionosulfites as well as their use as diatomic sulfur precursors. © 2007 Wiley Periodicals, Inc. 18:449–459, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20341

[1]  I. Abu-Yousef The organic chemistry of diatomic sulfur , 2006 .

[2]  D. N. Harpp,et al.  Crossover point between dialkoxy disulfides (ROSSOR) and thionosulfites ((RO)2S=S): prediction, synthesis, and structure. , 2006, Journal of the American Chemical Society.

[3]  D. N. Harpp,et al.  Generalized synthesis and physical properties of dialkoxy disulfides. , 2005, The Journal of organic chemistry.

[4]  J. Nakayama,et al.  The Chemistry of the Thiosulfinyl Group: Preparation, Structure, and Spectroscopic and Chemical Properties of Cyclic Thionosulfites , 2005 .

[5]  D. N. Harpp,et al.  Comparison of the structural properties of compounds containing the XSSX moiety (X = H, Me, R, Cl, Br, F, OR) , 2004 .

[6]  D. N. Harpp,et al.  Synthesis of new cyclic thionosulfites. , 2003, The Journal of organic chemistry.

[7]  J. Nakayama,et al.  The thiosulfinyl group serves as a stereogenic center and shows diamagnetic anisotropy similar to that of the sulfinyl group. , 2003, Journal of the American Chemical Society.

[8]  H. Gottlieb,et al.  Tandem sigmatropic rearrangements and cyclizations of propargylic dialkoxy disulfides , 2003 .

[9]  D. N. Harpp,et al.  Dialkoxy disulfides from cubycarbinols , 2002 .

[10]  J. Baldwin,et al.  Condensed thiophenes and selenophenes: thionyl chloride and selenium oxychloride as sulfur and selenium transfer reagents. , 2002, The Journal of organic chemistry.

[11]  K. Ingold,et al.  Laser Flash Photolysis Studies on the First Superoxide Thermal Source. First Direct Measurements of the Rates of Solvent-Assisted 1,2-Hydrogen Atom Shifts and a Proposed New Mechanism for This Unusual Rearrangement1 , 2000 .

[12]  G. Ballester,et al.  Discovery of gaseous S2 in Io's Pele plume. , 2000, Science.

[13]  A. McEwen,et al.  Io's thermal emission from the Galileo photopolarimeter-radiometer. , 2000, Science.

[14]  R. Flammang,et al.  Thiosulfoxides (X2SS) and disulfanes (XSSX) , 2000 .

[15]  Dianxun Wang,et al.  HeI photoelectron spectroscopic study of the electronic structure of SSF2 and FSSF compounds , 1998 .

[16]  Ruslan M. Minyaev,et al.  Theoretical study of O - > X (S, Se, Te) coordination in organic compounds , 1998 .

[17]  M. Cremonini,et al.  Conformational Studies by Dynamic NMR. 63.1 Stereodynamics of Dialkylamino Ethoxy Disulfides: S−S and S−N Rotation Processes , 1998 .

[18]  D. N. Harpp The Sulfur Diatomics: Generation and Trapping Chemistry , 1998 .

[19]  K. Ingold,et al.  Invention of the First Azo Compound To Serve as a Superoxide Thermal Source under Physiological Conditions: Concept, Synthesis, and Chemical Properties1 , 1997 .

[20]  D. N. Harpp,et al.  INHERENTLY HINDERED ROTATION ABOUT A DISULFIDE BOND , 1997 .

[21]  D. N. Harpp,et al.  Recent chemistry of the chalcogen diatomics , 1997 .

[22]  R. Borghi,et al.  Conformational Studies by Dynamic NMR. 60.1 Structure and Stereomutation of the Enantiomers of Dialkoxy Disulfides , 1997 .

[23]  D. B. Nash,et al.  VOLCANIC RESURFACING OF IO : POST-REPAIR HST IMAGING , 1997 .

[24]  S. Bottle,et al.  DIATOMIC SULFUR DETECTION BY BUTADIENE AND NORBORNENE: A CAUTIONARY NOTE , 1997 .

[25]  Alfred S. McEwen,et al.  Global Color Variations on Io , 1997 .

[26]  D. N. Harpp,et al.  Diatomic sulfur transfer from stable alkoxy disulfides , 1995 .

[27]  Paul von Ragué Schleyer,et al.  Theoretical investigation of the relative stabilities of XSSX and X2SS isomers (X = F, Cl, H, and CH3) , 1995, J. Comput. Chem..

[28]  H. Schmidt,et al.  Sulfur compounds. Part 173. Structure and Electron Density of Solid Dimethoxydisulfane, (CH3O)2S2 , 1994 .

[29]  H. Schmidt,et al.  STRUCTURE AND ELECRON DENSITY OF SOLID DIMETHOXYDISULFANE, (CH3O)2S2 , 1994 .

[30]  R. Gleiter,et al.  The Photoelectron Spectra of Dimethoxysulfane and Dimethoxydisulfane , 1993 .

[31]  J. E. Wood,et al.  Generation of diatomic sulfur by solution thermolysis of 2,3-dithiabicyclo[2.2.1]hept-5-ene , 1992 .

[32]  H. Schmidt,et al.  Gas-Phase Structure and Vibrational Spectra of Dimethoxydisulfane, (CH3O)2S2 , 1991 .

[33]  S. Firth,et al.  The microwave spectrum of the chain isomer of disulfur difluoride: FS-SF , 1991 .

[34]  Y. Gareau,et al.  Rearrangements and stereochemistry of sulfur additions to olefins , 1990 .

[35]  R. Steudel,et al.  The Retention of Six-, Seven-, Eight-, and Twelve-Membered Ring Molecules of Type SexS y in Reversed-Phase HPLC. Prediction of Retention for Unknown SexS y Heterocycles and Analysis of Sulfur-Selenium Melts , 1990 .

[36]  H. Willner,et al.  Fluorine-19 NMR chemical shift of sulfur difluoride in the gas phase , 1990 .

[37]  P. Schleyer,et al.  Chemical bonding in hypervalent molecules. The dominance of ionic bonding and negative hyperconjugation over d-orbital participation , 1990 .

[38]  H. Willner,et al.  The geometric structures of the disulphur difluoride isomers: an experimental and ab initio study , 1989 .

[39]  J. S. Francisco,et al.  The thermochemistry of polyoxides and polyoxy radicals , 1988 .

[40]  G. Mendenhall,et al.  Deuterium isotope cage effects in the dismutation of alkoxyl radicals. Significance for the mode of alkylperoxyl termination , 1985 .

[41]  D. N. Harpp,et al.  Molecular sulfur (S2): generation and synthetic application , 1984 .

[42]  N. N. Greenwood,et al.  Chemistry of the elements , 1984 .

[43]  P. Feldman,et al.  The discovery of S2 in comet IRAS-Araki-Alcock 1983d , 1983 .

[44]  Steven W. Martin,et al.  Decomposition rates, synthesis, and spectral properties of a series of alkyl hyponitrites , 1983 .

[45]  K. Turnbull,et al.  Compounds containing the sulfur-sulfur double bond , 1982 .

[46]  R. D. Baechler,et al.  Structural effects upon competitive decomposition pathways of Thiosulfoxide intermediates , 1981 .

[47]  F. Sauriol,et al.  Conformational studies of 7-membered cyclic sulfites. 3-oxo-2,4,3-dioxathiepin and 3-OxO-2,4,3- benzodioxathiepin , 1981 .

[48]  D. N. Harpp,et al.  Synthesis and X-ray crystal structure of O,O-bicyclohexyl-1,1′-diyl thiosulphite , 1980 .

[49]  F. Iwasaki The crystal and molecular structure of 2,4‐di‐tert‐butyl‐6‐methyl‐N‐thiosulphinylaniline , 1979 .

[50]  M. Feuerhahn,et al.  Infrared spectroscopic evidence for thiothionyl chloride and bromide in argon matrices at 9 K , 1979 .

[51]  I. V. Still,et al.  Thiophosphoryl bromide: a new reagent for the reduction of sulfoxides to sulfides , 1979 .

[52]  R. Bognár,et al.  DEOXYGENATION OF SULFOXIDES WITH BORON SULFIDE , 1979 .

[53]  I. V. Still,et al.  Reduction of Sulfilimines to Sulfides with Phosphorus Pentasulfide , 1978 .

[54]  I. V. Still,et al.  PHOSPHORUS PENTASULFIDE AS A MILD, SELECTIVE REAGENT FOR THE REDUCTION OF SULFOXIDES TO SULFIDES , 1978 .

[55]  W. Weber,et al.  Facile reduction of sulfoxides by disilthianes , 1978 .

[56]  K. Fukui,et al.  A Molecular-orbital Calculation of Chemically-interacting Systems. Interaction between Two Radicals. Self-reaction of Peroxyl Radicals , 1978 .

[57]  R. Cookson,et al.  Convenient synthesis of allenyl sulphides; application to the synthesis of αβ-unsaturated ketones , 1978 .

[58]  R. D. Baechler,et al.  The intermediacy of thiosulfoxides in deoxygenation of sulfoxides with P4S10 , 1978 .

[59]  R. D. Baechler,et al.  The conversion of allyl sulfoxides into allyl disulfides via the intramolecular rearrangement of thiosuifoxides , 1978 .

[60]  D. A. Long,et al.  In situ uv photolysis of disulphur dichloride in argon and nitrogen matrices: infrared spectroscopic evidence for thiothionyl chloride , 1978 .

[61]  I. V. Still,et al.  A GENERAL PROCEDURE FOR THE REDUCTION OF SULFOXIDES TO SULFIDES , 1977 .

[62]  S. Ōae,et al.  Mild and selective reduction of sulfoxides in the mixture with other sulfinyl compounds with trifluoroacetic anhydride-hydrogen sulfide system. , 1977 .

[63]  James P. Snyder,et al.  Lone pair-lone pair interactions in unsymmetrical systems: RSSR vs. RSOR , 1977 .

[64]  Ian Fleming,et al.  Frontier Orbitals and Organic Chemical Reactions , 1977 .

[65]  R. Micetich Convenient deoxygenation of penicillin and cephalosporin sulfoxides , 1976 .

[66]  R. D. Baechler,et al.  Reaction of allylic thioethers with elemental sulfur , 1973 .

[67]  T. Stroyer‐Hansen,et al.  Infrared spectra of S4 , 1972 .

[68]  J. D. Andose,et al.  Linear free energy correlations of barriers to pyramidal inversion , 1972 .

[69]  J. E. Bennett,et al.  The Self-Reaction of sec-Alkylperoxy Radicals: A Kinetic Electron Spin Resonance Study , 1972 .

[70]  S. Ōae,et al.  The reduction of semipolar linkages by O,O-dialkyl dithiophosphoric acid , 1972 .

[71]  S. Ōae,et al.  Reduction of semipolar sulphur linkages with carbodithioic acids and addition of carbodithioic acids to olefins , 1972 .

[72]  J. D. Andose,et al.  Semiempirical calculation of barriers to pyramidal inversion for first- and second-row elements , 1971 .

[73]  J. Baldwin,et al.  Thiosulfoxides. Intermediates in rearrangement and reduction of allylic disulfides , 1971 .

[74]  R. R. Fraser,et al.  Barriers to rotation about the sulfur-sulfur bond in acyclic disulfides , 1971 .

[75]  M. Raban,et al.  The validity of approximate equations for kc in dynamic nuclear magnetic resonance , 1971 .

[76]  F. Seel,et al.  PMR‐Spektren und Struktur von Alkyl„thiosulfiten”︁ , 1970 .

[77]  K. Ingold,et al.  ABSOLUTE RATE CONSTANTS FOR HYDROCARBON AUTOXIDATION. XVI. REACTIONS OF PEROXY RADICALS AT LOW TEMPERATURES , 1969 .

[78]  K. Mislow,et al.  Thermal racemization of diaryl, alkyl aryl, and dialkyl sulfoxides by pyramidal inversion , 1968 .

[79]  W. Neumann,et al.  Abfangreaktionen kurzlebiger Radikale, IV. Zum induzierten radikalischen Zerfall von Azoverbindungen RONNOR , 1968 .

[80]  R. W. Fessenden ESR Spectrum of a Trioxide Radical , 1968 .

[81]  Rd Brown,et al.  Synthesis, chemical properties, and U.V. spectra of thio-thionyl fluoride and difluorodisulphane , 1967 .

[82]  E. Miller,et al.  Mechanisms of Thermal Racemization of Sulfoxides1 , 1966 .

[83]  M. Dietrich,et al.  Organic Esters of Bivalent Sulfur. II. Branch-Bonded Sulfur Esters from 1,2-Diols and Sulfur Monochloride1 , 1965 .

[84]  M. Dietrich,et al.  Organic Esters of Bivalent Sulfur. I. Dialkoxy Disulfides , 1965 .

[85]  Q. Thompson Organic Esters of Bivalent Sulfur. III. Sulfoxylates , 1965 .

[86]  Carl R. Johnson,et al.  The Stereochemistry of Oxidation at Sulfur. Oxidation of 4-Substituted Thianes to Sulfoxides1 , 1965 .

[87]  F. Seel,et al.  Infrarot‐ und massenspektroskopische Untersuchungen an isomeren Dischwefeldifluoriden. Hinweise auf eine Molekülverbindung aus Difluordisulfan und Thiothionylfluorid , 1965 .

[88]  M. Dietrich,et al.  Thionosulfites. A New Class of Cyclic Esters Containing Branch-Bonded Sulfur , 1964 .

[89]  R. L. Kuczkowski The Mass and Microwave Spectra, Structures, and Dipole Moments of the Isomers of Sulfur Monofluoride , 1964 .

[90]  Carl R. Johnson,et al.  Equilibration of 4-Substituted Thiane 1-Oxides , 1964 .

[91]  K. Mislow,et al.  Stereoisomeric Thianthrene Sulfoxides. Configurational Assignments and Thermal Equilibrations , 1964 .

[92]  F. Seel,et al.  Über Dischwefeldifluorid (Thio‐thionylfluorid) , 1964 .

[93]  R. L. Kuczkowski SULFUR MONOFLUORIDE: THE MICROWAVE SPECTRUM OF A SECOND ISOMER , 1963 .

[94]  R. L. Kuczkowski,et al.  Microwave and Mass Spectra of Sulfur Monofluoride , 1963 .

[95]  P. Lauterbur,et al.  1012. The isomeric pentane-2,4-diol cyclic sulphites , 1963 .

[96]  G. M. Androes,et al.  The Activation Energy of Inversion in Substituted 1,2-Dithiane and 1,2-Dioxane Measured by the Nuclear Magnetic Resonance Technique1 , 1961 .

[97]  P. Lauterbur,et al.  Proton Magnetic Resonance, Structure and Stereoisomerism in Cyclic Sulfites , 1961 .

[98]  R. J. Myers,et al.  The microwave spectrum, structure, and dipole moment of disulfur monoxide , 1959 .

[99]  D. R. Douslin,et al.  2,3-dithiabutane, 3,4-dithiahexane, and 4,5-dithiaoctane: chemical thermodynamic properties from 0 to 1000/sup 0/K , 1958 .

[100]  G. Zinner Ester der Thioschwefligen Säure , 1957 .

[101]  Glen A. Russell,et al.  Deuterium-isotope Effects in the Autoxidation of Aralkyl Hydrocarbons. Mechanism of the Interaction of PEroxy Radicals1 , 1957 .

[102]  H. S. Gutowsky,et al.  Rate Processes and Nuclear Magnetic Resonance Spectra. II. Hindered Internal Rotation of Amides , 1956 .

[103]  S. Abrahams THE CRYSTAL AND MOLECULAR STRUCTURE OF ORTHORHOMBIC SULFUR , 1955 .

[104]  G. Brandt,et al.  410. Organometallic and organometalloidal fluorine compounds. Part III. Trifluoromethyl derivatives of sulphur , 1952 .

[105]  O. Hassel,et al.  The Prevalence of Unbranched Sulphur Chains in Polysulphides and Polythionic Compounds. , 1950 .

[106]  Hla Baw,et al.  144. Stereoisomerism of disulphoxides and related substances. Part IX. Disulphoxides in the thianthren series , 1934 .

[107]  A. Spong 111. The properties of the chlorides of sulphur. Part VIII. Changes of density on heating or irradiation , 1934 .

[108]  K. Fries,et al.  Über isomere Disulfoxyde des Thianthrens , 1911 .

[109]  F. Lengfeld Ueber die Ester der Säure H2S2O2 (Thionschwefligesäure , 1895 .