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University Microfilms International 300 N INFORMATION TO USERS This was produced from a copy of a document sent to us for microfilming. While the most advanced technological means to photograph and reproduce this document have been used, the quality is heavily dependent upon the quality of the material submitted. The following explanation of techniques is provided to help you understand markings or notations which may appear on this reproduction. 1. The sign or “target” for pages apparently lacking from the document photographed is “Missing Page(s)”. If it was possible to obtain the missing page(s) or section, they are spliced into the film along with adjacent pages. This may have necessitated cutting through an image and duplicating adjacent pages to assure you of complete continuity. 2. When an image on the film is obliterated with a round black mark it is an indication that the film inspector noticed either blurred copy because of movement during exposure, or duplicate copy. Unless we meant to delete copyrighted materials that should not have been filmed, you will find a good image of the page in the adjacent frame. 3. When a map, drawing or chart, etc., is part of the material being photo­ graphed the photographer has followed a definite method in “sectioning” the material. It is customary to begin filming at the upper left hand corner of a large sheet and to continue from left to right in equal sections with small overlaps. If necessary, sectioning is continued again—beginning below the first row and continuing on until complete. 4. For any illustrations that cannot be reproduced satisfactorily by xerography, photographic prints can be purchased at additional cost and tipped into your xerographic copy. Requests can be made to our Dissertations Customer Services Department. 5. Some pages in any document may have indistinct print. In all cases we have filmed the best available copy. University Microfilms International 300 N. ZEEB ROAD, ANN ARBOR, Ml 48106 18 BEDFORD ROW, LONDON WC1 R 4EJ, ENGLAND 8008782 POFFENBERGER, CRAIG ALAN SYNTHESIS AND CHEMISTRY OF NOVEL SULFUR-OXIDE LIGANDS IN ORGANOMETALLIC COMPLEXES The Ohio State University Ph.D. 1979 University Microfilms in tern et lO nel 300 N. Zeeb Road, Ann Arbor, MI 48106 18 Bedford Row, London WCIR 4EJ, England SYNTHESIS AND CHEMISTRY OF NOVEL SULFUR-OXIDE LIGANDS IN ORGANOMETALLIC COMPLEXES DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By Craig Alan Poffenberger, B.S. ***** The Ohio State University 1979 Reading Committee: Approved By Dr. Andrew Wojcicki Dr. Sheldon Shore Advisery Dr. Devon Meek Department of Chemistry ACKNOWLEDGEMENTS I wish to express my sincere gratitude for the support and encouragement of my family and my wife, Kathy, throughout the course of this endeavor. I am particularly indebted to Dr. Andrew Wojcicki for his advice and guidance during this research effort and in the preparation of this work. I am grateful to my fellow graduate students and friends for their assistance in technical and non-technical concerns. I also wish to thank Vicki Faustini for typing this manuscript. Finally, I wish to acknowledge the Chemistry Department of The Ohio State University and the National Science Foundation for their financial support. ii VITA July 15, 1951........ Born - Rockford, Illinois 1973 ................ B.S., University of Illinois, Urbana, Illinois 1973-1979............ Teaching and Research Assistant, The Ohio State University, Columbus, Ohio PUBLICATIONS C. A. Poffenberger and A. Wojcicki, " Reactivity of the Alkylsulfite Ligand in u'-CsHsFeCCO)2 S (0)aOR. " Paper presented to the 1979 11th Central Regional Meeting of the American Chemical Society, Ohio State University, Columbus, Ohio, May 7-9, 1979. C. A. Poffenberger and A. Wojcicki, " Alkylsulfito, Bisulfito, and Sulfito Complexes of r^-Cyclopentadienyldicarbonyliron(II)," J. Organometal. Chem., 165, C5(1979). Craig A. Poffenberger, and Andrew Wojcicki, " Preparation and Properties of the Alkylsulfito Complexes (n^-C5H5)Fe(C0)2S(0)20R. " Paper presented to the 1978 Joint Central-Great Lakes Regional Meeting of the American Chemical Society, Butler University, Indianapolis, Indiana, May 24-26, 1978. N. H. Tennent, S. R. Su, C. A. Poffenberger, and A. Wojcicki, " Synthesis of a Transition Metal Dithionite Complex, (n^-CsHs)(CO)2Fe-S(0)2-S(0)a-Fe(CO)2 (u^-CsHs), " J. Organometal. Chem., 102. C46(1975). D. J. Sepelak, C. G. Pierpont, E. K. Barefield, J. T. Budz, and C. A. Poffenberger, " Organometallic Chemistry of the Carbon-Nitrogen Double Bond. 1. Nickel Complexes Prepared from Iminium Cations and the X-Ray Structure of [(C6Hs)3P]Ni[CH2N(CH3 )2 ]Cl,'* J. Am. Chem. Soc., 98, 6178(1976). FIELDS OF STUDY Major Field: Inorganic Chemistry, Professor Andrew Wojcicki iii TABLE OF CONTENTS Page ACKNOWLEDGEMENTS.......... ii VITA ........................................................ iii LIST OF T A B L E S.............................................. v LIST OF FIGURES.............................................. vii INTRODUCTION ................................................ 1 EXPERIMENTAL ................................................ 19 I. Reagents and Solvents.............................. 19 II. Instrumental and Physical Methods.................. 22 III. General Experimental Procedures.................... 23 IV. Literature Preparations............................ 24 V. The Preparation, Characterization, and Reactions of Some New Sulfur-Oxide Ligands in Organo-Transition Metal Complexes .............. 25 RESULTS AND DISCUSSION ...................................... 86 I. Organo-Transition Metal-Dithionite Complexes .... 86 II. Organo-Transition Metal-Alkylsulfito Complexes . 113 III. Preparation of Transition Metal Complexes of the Ethyl Methanesulfinate Ligand.................. 152 SUMMARY........ ,............................................. 160 CONCLUDING REMARKS .......................................... 163 APPENDIX..................................................... 165 BIBLIOGRAPHY ................................................ 174 iv LIST OF TABLES Table Page 1. Reactions of [r|®-CsHsFe(C0)2S0a]2 and RX................ 46 2. Infrared Spectra of the Transition Metal Dithionite Complexes, Diphenyl-«~disulfone, and Sodium Dithionite. 87 3. Comparison of v(CO) and vCSOg) Absorptions for [n^-CsHsFeCCOaJaSOa and [n^-CsHsFeCCOaSOaJa.......... 91 4. Ultraviolet-Visible Spectra of Selected Metal Carbonyl Dimers ........................................ 96 5. Ultraviolet-Visible Spectra of [n^-C5HsFe(C0)aS0a]2, [^^"CsHsFe(CO)a]aSOa» snd [Mn(CO)gSOa]a from 2700 Â to 6000 Â. ................................ 108 6. Important Stretching Frequencies in r)^-CsH5Fe(C0)aS(0)a0R and Other Metal-Alkylsulf ito Complexes.................. 116 7. Comparison of V(C0) and v(SOa) Absorptions for n^-CsHsFeCCOaSCOaCHa and n^-CsHsFeCCO) aS(0) aOCHa • • • • 118 8. NMR Spectra for n^-CsHsFe(CO)aS(0)aOR................ 119 9. NMR Spectra for MEn^-CgHsFe(CO)aSOa] ................ 137 10. Important Stretching Frequencies in [n^-CsHsFe(CO)a(SO(OCaHg)(OR))]PFe Complexes, r|^-CsHsFe(CO)aS(0)aOR Complexes, and OS(OCaHs)a........ 146 11. NMR Spectra of [r)^-C5HsFe(C0)a (SO(OCaHs ) (OR) ) ]PFe Complexes and 0S(0CHaCHg)2.............................. 148 12. Comparison of Important Stretching Frequencies of [n®-CsHsFe(C0)(L)(S0(0CaH5)(CH3))]PF6 Complexes and ri'-CsHsFe^CO) (L)S (O)aR Complexes.................... 154 13. NMR Spectra for [n^-C5HsFe(C0)(L)(SO(OCaHs)(CHg))]PFe, n“-C5HsFe(C0)(L)S(0)a0R, and OS(OCaHs)(CHg) ............ 158 V LIST OF TABLES (contd.) Figure Page 14. Major Mass Spectral Peaks for [n'-CsHsFeCCOjzSOajz. 166 15. Major Mass Spectral Peaks for [Mn(CO)5 SO2 ]2 ............ 167 16. Major Mass Spectral Peaks for [Re(C0 )5 S0 2 ]2 ............ 168 17. Major Mass Spectral Peaks for Compound " A " ............ 169 18. Major Mass Spectral Peaks for (ri*-CsH5 )2Mo 2 S202 ........ 170 19. Major Mass Spectral Peaks for (ri*-C5H 5 )2W 2 S2 0 2 .......... 171 20. Major Mass Spectral Peaks for [ (n*-C5H 5 )3Fe3 (CO)^S]BFi, (n = 4 or 5 ) ..................... 172 21. Major Mass Spectral Peaks for ri°-CsH5 Fe(C0 )2 S(0 )2 0 R . 173 VI LIST OF FIGURES Figure Page 1. Apparatus for Photolysis of [M]g and SO2 at 20°C........ 29 2. Apparatus for Photolysis of [M]z and SO2 at -10°C .... 33 3. Apparatus for the Collection of Gases from Photolysis of [n*-C3HsW(C0 )3 ]2 and SO2 ............................ 39 4. Titration Curve for the Neutralization of a 10 mL Aliquot of a Solution of 0.0331g of ri’*-C5HsFe(C0 )2 S(0 )2 0 H in 25 mL of H 2O with 0.04992 M N a O H .................... 78 5. Infrared Spectrum (Nujol) of [ri'-CsHsFe(CO) 2 8 0 2 1 2 in A) the 2100 to 1900 cm~^ Region and B) the 1300 to 900 cm“ ^ R e g i o n........................................ 8 8 6. Infrared Spectra (Nujol) of A) [Mn(C0)sS02]2 and B) [Re(CO)5 SO2 ]2 in the 1300 to 900 cm“ ^ Region ........ 98 7. Infrared Spectra of A) [Mn(C0 )sS0 2 ]2 in CH2 CI2 , B) Mn(CO)sBr in CHCI3 , and C) Mn(C0)5S(0)2CH2C6H5 in CHCI3 in the 2200-1900 cm"‘ R e g i o n .................. 101 8. Infrared spectrum (KBr) of ri*“CsHsFe(CO) 28(0)200113 in the 2100-1900 cm~^ and 1300-800 cm“ ^ Regions........ 117 9. NMR Spectrum of Tl®-C5H 5 Fe(C0 )2 8 (0 )a0 CH(CH3)2 in CDCI3 with TMS as Internal S t a n d a r d ..................... 121 10. Infrared Spectrum (KBr) of r|“-C5HsFe(C0 )2 8 (0 )2 0 H in the 1300-700 cm“ ^ R e g i o n ............................ 131 11. Infrared Spectrum (KBr) of Na[ri^-CsH5Fe(C0)2803]
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