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University International 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 o f complete continuity. 2. When an image on the Him 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 Aimed, you will And 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 deAnite method in “sectioning” the material. It is customary to begin Aiming at the upper left hand comer 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 Arst 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 Aimed the best available copy. University Micrdrilms International 300 N. ZEEB ROAD. ANN ARBOR, Mt 48106 18 BEDFORD ROW. LONDON WC1R 4EJ, ENGLAND 7922533 MUTHARD, JEAN LOUISE SYNTHESIS AND CHEMISTRY OF TOP.OLOG 1C ALLY UNUSUAL POLYQUINANES. THE OHIO STATE UNIVERSITY, PH.D., 1979 University Microfilms International 3 0 0 n. z e e b r o a d, a n n a r b o r, mi ab io g SYNTHESIS AND CHEMISTRY OF TOPOLOGICALLY UNUSUAL FOLYQUINANES DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By Jean Louise Muthard, B.S. ***** The Ohio State University 1979 Reading Committee: Approved By Dr. Leo A, Paquette Dr. John A. Secrist, III Dr. John S. Swenton Q u a g . C S Adviser Department of Chemistry To my family ACKNOWLEDGMENTS The author is grateful to Professor Paquette for his guidance as a research adviser and his boundless enthusiasm as a chemist. She is extremely indebted to the many graduate students, postdoctoral fellows, and friends who have been supportive on both the emotional and intellectual levels during her time at The Ohio State University. Special thanks are extended to Dr. Morey Osborn and Dr. Michael Geckle for their unselfish assistance in obtaining many of the carbon magnetic resonance spectra reported here. The chemical contri­ butions of Dr. Tadeusz Cynkowski, Dr. Otto Schallner, Dr. Robert Snow, Dr. Matthew Wyvratt, Dr. Richard Bartetzko, Professor Rolf Gleiter, and Professor Gary Christoph are gratefully acknowledged. Though the existence of Matthew Wyvratt has at times made the last few years more difficult, his encouragement and understanding have been invaluable in the completion of this work. The author expresses the deepest appreciation to Matt, her husband. iii VITA May 25, 1953 ........... Born, Atlanta, Georgia 1974 .................... B.S., high honors, University of Florida, Gainesville, Fla. 1 9 7 4 - 1 9 7 5 ........... University Fellow, The Ohio State University, Columbus, OH 1975 - 1977.. ........... Research Assistant, Department of Chemistry, The Ohio State University, Columbus, Ohio 1977 - 1978 ........... Dissertation Fellow, The Ohio State University, Columbus, OH 1978 - 1979 ........... Research Assistant, Department of Chemistry, The Ohio State University, Columbus, OH PUBLICATIONS "C^g-Hexaquinacene, 11 L.A. Paquette, R.A. Snow, J.L. Muthard, and T. Cynkowski, J. Am. Chem. Soc., 100, 1600 (1978). "Long Range Electronic Transmission in Conformationally Rigid ar-Diketones, " R. Bartetzko, R. Gleiter, «T- L. Muthard, and L.A. Paquette, J. Am. Chem. Soc., 100, 5589 (1978). "Quantitative Assessment of pp-cr Overlap in a Topologically Convex Triene. Electronic and Crystal Structure Analysis of C 1 6 -Hexaquinacene." G.G. Christoph, J.L. Muthard, L.A. Paquette, M.C. Bohm, and R. Gleiter, J. Am. Chem. Soc., 100, 7782 (1978). FIELD OF STUDY Major Field: Organic Chemistry iv TABIiE OF CONTENTS Page DEDICATION ........................................... ii ACKNOWLEDGMENTS. ■ . ................................ iii VITA .................................................. iv LIST OF TABLES ...................................... vi LIST OF FIGURES ...................................... vii LIST OF SCHEMES .................................... ix INTRODUCTION . .................................. 1 RESULTS AND DISCUSSION ............................. Part I. The Electronic Structure and Chemistry of Some Conformationally Rigid (y-Dfketones........................... 8 Part II. Synthesis and Chemistry of a C 2 Symmetric Bislactone ................ 43 Part III. C^g-Hexaquinacene.................... 61 EXPERIMENTAL ......................................... 108 APPENDIXES A. Selected Proton Magnetic Resonance Spectra 158 B. Carbon Magnetic Resonance Spectra of Triols 115 and 1 1 6 .................................. 170 REFERENCES ..............................................172 v LIST OF TABLES Table Page 1. Comparison Between Measured Vertical Ionization Potentials# Iy j, of 28, 29, 22, and 30_ and Calculated Orbital Energies (e^) 24 2. Measured and Calculated Electronic Absorption Spectra of 28, 29, 22, and 30_................ 28 3. Emission Data of Compounds 28, 29, 22, and 3<3 32 1 3 4. C NMR Spectral Parameters for Hexaquinacene .................................. 77 5. pp—o Overlap Integrals Estimated Using Slater O r b i t a l s ...................................... 83 LIST OF FIGURES Figure Page 1 . PE Spectra of 28, 29, 22, and 3(3 Between 8 and 16 e V .................................... 23 2. Correlation Between the First Bands of the PE Spectra of 22, 29, 28, and 30^ Based on MINDO/3 Calculations .................. 26 3. Comparison Between the First Bands in the Electronic Absorption Spectra of 28, 29, 22, and 30^ in Methylene Chloride........... 30 4. Comparison of the Orbital Energies for 28 without (left) and with (right) TT* - 17* Interaction ....................... ..... 32 5. Orbital Alignments of 1,4-Diketones .... 44 6 . Orbital Alignment Present in 5j5............ 46 7. Orbital Alignments Present in 1,4-Diketones 78 (A) and 77 (B) ......................... 69 8 . X-Ray Crystal Structure of C --Hexaquinacene ( 2 4 ) ......................... 80 9. View of C.g-Hexaquinacene (24) Down the Three-fold axis ........................ 81 10. The He(I) Photoelectron Spectrum of C -- Hexaquinacene (24)...................... 84 11. Orbital Energy Plot Showing the Variations in e(Il) and ai(ll) Levels as a Function of Distance Between Interacting II Bonds . 8 6 12. Correlation of the Ionization Energies of 24, 95, and 96........................... 87 vii FIGURES (CONT'D) Figure Page 13. X-Ray Crystal Structure of C .. ,-Hexaquinane ( 9 4 ) ......................... .................. 8 8 14. Depiction of the Intramolecular Hydrogen- Hydrogen Distances in 9 4 ....................... 89 15. Vacuum Pyrolysis Apparatus ................... 98 viii LIST OF SCHEMES Scheme Page I. Synthesis of Diketones 22, 29, and 30^ . 20 II. Synthesis of Biscyclopentenone 55_ .... 45 III. Reductive Fragmentation of Enone S5 . 47 IV. Attempted Ring Contraction of Bislactone 6 0 ........................................... 53 V. Attempted Synthesis of 24 from 84 .... 72 VI. Thermolysis of Triquinacene (95) ......... 97 VII. Hydroboration of C^-Hexaquinacene (24). 102 ix INTRODUCTION The chemistry of six-membered ring annulation reactions has been thoroughly studied due to the early interest in steroid chemistry. The construction of polyquinanes, fused five-membered ring compounds/ has received increased attention only over the past decade. The development of synthetic methodology in this area has been motivated, in part, by the recognition of the .medicinal importance of prostaglandins and the isolation of natural products possessing polyfused cyclopentanoid structures. Interest has also grown in the construction of higher polyquinanes with an all syn-cis stereochemistry which lends them a sphere-like topology. The optimal arrangement of fused cyclopentane rings in the spherical pentagonal dodecahedrane (1 ) has not yet been realized. 1 1 The majority of the early attention in the polyquinane field was directed toward the synthesis and chemistry of the diquinane, bicyclo[3.3.0]octane ( 2 ). The parent hydrocarbon and its functionalized derivatives 2 were prepared by utilizing such methods as the Dieckmann cyclization, vinyl cyclopropane rearrangements/ and transannular chemistry of cyclooctadiene and cyclooctane derivatives. Among the triquinanes are the carbon skeletons of several natural products including hirsutic acid C (3)/^ 2 3 the coriolin 4/ and hirsutine (5). Eaton and coworkers 4 have synthesized a cis, syn, cis
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