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The Synthesis of Azulenes by the (6+4) Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1977 The yS nthesis of Azulenes by the (6+4) Cycloadditions of 6-Aminofulvenes to Thiophene- S,s-Dioxides. Stephen Elliott Reiter Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Reiter, Stephen Elliott, "The yS nthesis of Azulenes by the (6+4) Cycloadditions of 6-Aminofulvenes to Thiophene-S,s-Dioxides." (1977). LSU Historical Dissertations and Theses. 3164. https://digitalcommons.lsu.edu/gradschool_disstheses/3164 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. INFORMATION TO USERS This material war produced from a microfilm copy of the original document. 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 original submitted. The following explanation of techniques is provided to help you understand markings or patterns 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 thru an image and duplicating adjacent pages to insure you complete continuity. 2. When an image on die film is obliterated with a large round black mark, it is an indication that the photographer suspected that the copy may have moved during exposure and thus cause a blurred image. You will finda good image of the page in the adjacent frame. 3. When a map, drawing or chart, etc., was part of the material being photographed the photographer followed a definite method in "sectioning" the material. It is customary to begin photoing at the upper left hand corner of a large sheet and to continue photoing from left to right in equal sections with a small overlap. If necessary, sectioning is continued again — beginning below the first row and continuing on until complete. 4. The majority of users indicate that the textual content is of greatest value, however, a somewhat higher quality reproduction could be made from "photographs" if essential to the understanding of the dissertation. Silver prints of "photographs" may be ordered at additional charge by writing the Order Department, giving the catalog number, title, author and specific pages you wish reproduced. 5. PLEASE NOTE: Some pages may have indistinct print. Filmed as received. University Microfilms International 300 North Zeeb Road Ann Arbor, Michigan 48106 USA St. John’s Road, Tyler's Green High Wycombe, Bucks, England HP10 8HR 78-7555 REITER, Stephen Elliott, 1950- THE SYNTHESIS OF AZULENES BY THE [6+4] CYCLOADDITIONS OF 6-AMINOFULVENES TO THIOPHENE-S,S-DIOXIDES. The Louisiana State University and Agricultural and Mechanical College, Ph.D., 1977 Chemistry, organic University Microfilms Internationalt Ann Arbor, Michigan 48106 THE SYNTHESIS OF AZULENES BY THE [6+4] CYCLOADDITIONS OF 6-AMINOFULVENES TO THIOPHENE-S,S-DIOXIDES A Dissertation Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Doctor of Philosophy in The Department of Chemistry by Stephen Elliott Reiter B.S., University of Florida, 1972 December, 1977 to Diane ACKNOWLEDGEMENT The author is grateful for the opportunity to have studied under the direction of Dr. Kendall N. Houk, whose tireless guidance, encouragement and tutelage have been instrumental to the execu­ tion and completion of this work. Gratitude is expressed for the many warm and lasting friend­ ships formed while at Louisiana State University. They have made graduate study an enjoyable experience. Many thanks. Financial support from the National Science Foundation, National Institutes of Health-Institution of General Medical Sciences, the Cities Service Research and Development Company, and the Dr. Charles E. Coates Memorial Fund of the Louisiana State University Foundation donated by George H. Coates is gratefully acknowledged. iii TABLE OF CONTENTS Page Acknowledgement ..................................................... iii List of Tables ....................................................... vii List of Figures ...................................................... viii A b s t r a c t .............................................................. ix I. Introduction .................................................... 1 A. Azulenes ........................................ 2 B. Thiophene Dioxides ......................................... 19 1. Synthesis ............................................... 19 2. Reactions ........................ 21 C. Fulvenes ................................................... 24 1. Theoretical Rationales of Periselectivity ........... 24 2. Synthesis of Arainofulvenes ........................... 28 3. Reactions of Aminofulvenes ........................... 29 II. Results and Discussion ........................................ 32 A. Preparation of Thiophene Dioxides ....................... 33 1. The Diene-Sulfur Dioxide Reaction ................. 33 2. Bromination of Sulfones ............................ 36 3. Dehydrobromination of 3,4-Dibromotetrahydro- thiophene Dioxides .................................... 38 B. Preparation of Aminofulvenes ............................. 41 C. Reactions of Thiophene Dioxides and Aminofulvenes . 45 1. Symmetrical Thiophene Dioxides ...................... 45 2. 3-Substituted Thiophene Dioxides .................... 62 3. 2-Substituted Thiophene Dioxides .................... 73 lv Page 4. 2,4-Dimethyl thiophene D i o x i d e ...................... 77 5. Reactions of Fulvene 5 ................... 81 6. Discussion ............................................ 90 a. Mechanism of Reaction .......................... 90 b. Reactivity ....................................... 94 c. Regioselectivity................................. 98 D. Conclusions ................................................ 102 III. Experimental .................................................. 104 A. Introduction ........................................ 104 B. Starting Materials .................................... 105 1. Syntheses of Thiophene Dioxides .................... 105 2. Syntheses of 3,4-Dibromotetrahydrothiophene Dioxides .................... ...... 105 3. Syntheses of 2 ,5-Dihydrothiophene Dioxides .... 106 4. Syntheses of Aminofulvenes ...........................110 C. Cycloadditions of Aminofulvenes and Thiophene D i o x i d e s .................................................. 112 1. Cycloaddition Reactions of 6-Dimethylamino- f u l v e n e ................................................ 113 2. Cycloaddition Reactions of 6-Methyl-6-dimethyl- aminofulvene ........................................ 115 3. Cycloaddition Reactions of Bis-6,6(dimethylamino) f u l v e n e . ; .............................................. 117 4. Cycloaddition Reactions of 3,6-Dimethyl-6- dimethylaminofulvene (5 ) .............................. 120 v Page 5. Attempted Cycloadditions of 6-Phenyl-6-dimethyl- aminofulvene ........................................ 125 6 . Attempted Cycloadditions of Fulvene 4 ............... 125 R e f e r e n c e s .............................................................126 A p p e n d i x ............................................................... 135 V i t a ................................................................... 140 vi LIST OF TABLES Table Number Page I 100 MHz nmr data for substituted azulenes .............. 48 II Calculated and observed shifts in the visible spectra of alkylsubstituted azulenes ........................... 53 III Calculated and observed shifts in the visible spectra of heterosubstituted azulenes . 54 IV Uv/vis data for substituted azulenes in hexane, V Summary of cycloaddition reactions carried out in this s t u d y ................................................. 103 VI Preparation of dibromotetrahydrothiophene dioxides from dienes ................................................. 107 VII Analytical data for new starting materials .............. 109 VIII Aminofulvene preparations ................................ Ill IX Cycloaddition reactions of 6-dimethylaminofulvene and thiophene dioxides .................................. 114 X Cycloaddition reactions of 6-methyl-6-dimethylamino- fulvene and thiophene dioxides ......................... 116 XI Cycloaddition reactions of 6,6-bis(dimethylamino) fulvene and thiophene dioxides ......................... 119 XII Cycloaddition reactions of 3,6-dimethyl-6-dimethyl- aminofulvene and thiophene dioxides .................... 121 XIII Elemental analyses of new azulenes ....................... 122 XIV Principal infrared absorptions of new azulenes .... 123 vii LIST OF FIGURES Figure Number Page 1 Bicyclo[5,3.0]decanones from elaborated cyclo- pentane and cycloheptane ............................. 5 2 Ziegler-Hafner synthesis of azulene .................. 6 3 Preparation of 4-substituted azulenes ................ 8 4 Preparation of thiophene-S,S-dioxide ................ 19 5 Dimerization of thiophene dioxides .................
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