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Preparation and Properties of Benzotropones and Benzohomotropones

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Preparation and Properties of Benzotropones and Benzohomotropones Western Michigan University ScholarWorks at WMU Dissertations Graduate College 8-1979 Preparation and Properties of Benzotropones and Benzohomotropones Robert E. Suder Western Michigan University Follow this and additional works at: https://scholarworks.wmich.edu/dissertations Part of the Organic Chemistry Commons Recommended Citation Suder, Robert E., "Preparation and Properties of Benzotropones and Benzohomotropones" (1979). Dissertations. 2697. https://scholarworks.wmich.edu/dissertations/2697 This Dissertation-Open Access is brought to you for free and open access by the Graduate College at ScholarWorks at WMU. It has been accepted for inclusion in Dissertations by an authorized administrator of ScholarWorks at WMU. For more information, please contact [email protected]. PREPARATION AND PROPERTIES OF BENZOTROPONES AND BENZOHOMOTROPONES Robert E. Suder A Dissertation Submitted to the Faculty of The Graduate College in partial fulfillment • of the Degree of Doctor of Philosophy Western Michigan University Kalamazoo, Michigan August 1979 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ACKNOWLEDGEMENTS The author wishes to express his appreciation to Dr. Harmon, Dr. Iffland, Dr. Howell, Dr. Nagler, and Dr. Derby for allowing him to complete the degree. A special thanks goes to Dr. Harmon for his guidance, inspiration, and incouragement. Invaluable assistance has come from the Department of Chemistry at Western Michigan University for the teaching associateship, and from the National Cancer Foundation for the research fellowship. Robert E . Suder Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. INFORMATION TO USERS This was produced from a copy of a document sent to us for microfilming. 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ANN ARBOR, Ml 48106 18 BEDFORD ROW. LONDON WC1R 4EJ, ENGLAND Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. !5UDER» ROBERT EDWIN PREPARATION AND PROPERTIES OF BENZOTROPQNES AND BENZOHOHOTROPONES. WESTERN MICHIGAN UNIVERSITY. PH.D., 1979 Univt M. International 300 n.zeeb road,ann arbor,mi w oe Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. TABLE OF CONTENTS page INTRODUCTION .................................... 1 BACKGROUND ...................................... 3 Tropylium Ions ............................. 3 Tropones and Benzotropones ............... 6 Homotropones and Homotropylium Ions ........ 7 DISCUSSION ..................................... 12 Polymethylenebenzotropones ................. 12 Bispolymethylenedibenzotropones ............ 18 Benzohomotropones .......................... 25 Tropolone Derivatives ...................... 31 EXPERIMENTAL .................................... 34 Preparation of Benzotropones and Benzo- tropylium Ions ................ 34 Preparation of Bispolymethylenedibenzo- tropones ......... 49 Preparation of Benzohomotropones ........... 57 Preparation of Tropolone Derivatives ....... 62 CONCLUSION ...................................... 65 BIBLIOGRAPHY .................................... 67 iii Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. INTRODUCTION Interest in tropones (1) and tropolones {2) has increased recently because many of their derivatives have been found to exist as natural products. 1 2 These include secondary vegetable metabolites such as stipitatonic (3.)1 and puberulic (^t)2 acids, as well as sepedonin (5)-^ .OH .OHHO, H0- .OH HO HO ■CH. 5 1 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. A number of alkyl tropolones, such as nookatinol (6), Zj, have been found in the heartwood of various Cupressales. Alkalodial tropolone derivatives, notably colchicine (2), have been found in plants of the lilacee.^ NHCOCH CH„0 7 Troponodial derivatives frequently show biological activity. One of the more interesting cases is the fungicidal activity of the tropolones of the Thu.ia trees, which effectively preserve their wood.^ Also, antimiotic activity is found in various colchicine Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. BACKGROUND Tropylium Ions In 1931 Huckel proposed that the tropylium ion, C^Hr7+, should possess aromatic character.® In fact, the tropylium ion was prepared in I89I by M e r l i n g , ^ but was not identified. His work was repeated in 195^ and the yellow solid .that was isolated was proven to be tropylium bromide (8).10 n Br— /x^ vvvBr // \\ been able to prepare various types of tropylium salts by hydride exchange between cycloheptatrienes and tri- (c 6h 5 )3c +y - (c6h 5)3c -h 3 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. A number of benzotropylium ions have also been prepared. The first isolation of one of these compounds lA was accomplished by Rennhard in 1955- He treated the benzotropone (£) with lithium aluminum hydride to afford the hydroxy compound (10), which upon addition of 70$ perchloric acid produced 11, a yellow solid. LiAlHi HClOi 11 One of the more extensively studied benzotropolone derivatives is that obtained from the methylation of the natural product purpurogallin (12), and this has led to the tropylium ion. 12 13 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. 5 Eschenmoser. and’ coworkers were able to isolate the tropylium hexachloroplatinate salt (1^) by first reducing the carbonyl function of 12 with lithium aluminum hydride and then treating the resulting alcohol with hexachloroplatinic acid. ^ LiAlHi The perchlorate salt has also been prepared using a similiar procedure. Proton NMR studies show the positive charge is delocalized over both rings. The methoxyl protons in Ik are shifted about 2k Hz further downfield, compared to 12* This downfield chemical shift is attributed to the delocalized positive charge, which decreases electron density, decreasing shielding. ^ Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Tropones and Benzotropones On the basis of proton NMR studies, it can be concluded that tropone (1) is planar and has bond alteration.^ Also, the IR spectrum shows the carbonyl absorption at 159^ cm-1, which is consistent for a conjugated system.1® Finally, the resonance stabilization energy of tropone is 1^ kcal mol ~1, whereas for cyclo- —1 19 heptatriene it is only 8 kcal mol . 7 X-ray crystallographic analysis of i|-,5-benzo- tropone (1^) show that it is almost planar, the carbonyl oxygen and the carbonyl carbon being displaced by 0.2 0 20 and 0.1 A, out of plane respectively. The IR carbonyl absorption is at 1590 cm-1, which is expected for a 21 conjugated ketone. Kloster-Jensen and coworkers were able to confirm that the tropone ring is reasonably planar by forcing the tropone ring out of planarity by a polymethylene bridge. A series of 6,8-polymethylenebenzotropones (16.) were prepared and it was found that the tropone ring is planar only if n ^ 7*21 0 15 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. (endo)H 17 It can be seen that the carbon-carbon -rr bond has been replaced by a methylene bridge forming a cyclopropane ring. Proton NMR studies of this compound clearly.in­ dicate the absence of any ring current.2^ The difference in the chemical shift between the endo and exo protons is only 0.5 Hz. The presence of a ring current would, of course, result in a greater difference in chemical shift of these protons, as seen in the
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