by Mei-Sing Ho. / Thesis (M.Phil.)--Chinese University of Hong Kong, 1989. / Bibliography: leaves 54-57.

Rozprawa habilitacyjna--Warsaw. / Polish and English. Includes bibliographical references (p. 20).

2-Alkyltetrahydroftirans have been prepared from C10-C18 primary alcohols. Complete characterisation of these compounds by mass spectral and NMR studies has been achieved. Ring-opening reactions of the 2-alkyltetrahydrofurans have been studied and have provided an insight into the chemistry of these compounds, highlighting differences in reactivities and reaction products compared with the parent molecule, tetrahydrofuran. The C10-C18 2-alkyltetrahydrofurans have been subjected to a variety of ring cleavage reactions involving reaction with Lewis acids and/or acyl halides to produce compounds of the type; RCH(X)CH2CH2CH2-Y and RCH(Y)CH2CH2CH2-X R = C6H29 - C14H29, X = halogen atom, Y = acyl group This work has demonstrated the ease with which these compounds may be ring opened. In some cases the reaction with the 2-alkyltetrahydrofiirans was observed to be more rapid and vigorous than with tetrahydrofuran itself. This was not always the case: The acid catalysed reaction of tetrahydrofiaran with dodecanol resulted in formation of the diether shown below, and a diester was similarly formed by the acid catalysed reaction of tetrahydrofliran with lauric acid. R0(CH2)4OR diether (R = C12H25) RCOO(CH2)4OCOR diester (R= C1H23) The analogous reactions with substituted tetrahydrofurans were slow and diether/diester yield was extremely low. Introduction of the alkyl group at position two of the tetrahydrofuran ring severely impeded the reaction. Instead the hydroxy ethers shown below were the major cyclic ether derived products. C12H25-O-CH(R)(CH2)3-OH and C12H25-O-(CH2)3CH(R)-0H. (R = C6H13) Oxidation of the 2-alkyltetrahydrofurans was readily achieved by treatment with ruthenium tetroxide and resulted in formation of the corresponding alpha-alkyl-gamma-lactones and gamma-keto acids in almost quantitative yields and RCO(CH2)2COOH (R=C6H13-C14H29).

by Zhi Zhong Song. / Thesis (Ph.D.)--Chinese University of Hong Kong, 1994. / Includes bibliographical references (leaves 158-171 (1st gp)). / Acknowledgements --- p.i / Contents --- p.ii / Abstract --- p.viii / List of Publications Based on Research Reported in this Thesis --- p.ix / List of Acronyms and Abbreviations --- p.x / Chapter Chapter I. --- The Reaction and Synthesis of Furans / Chapter I.1. --- Introduction --- p.1 / Chapter I.2. --- General Survey of Reaction of Furan --- p.2 / Chapter I.2.1. --- Electrophilic substitutions --- p.2 / Chapter I.2.2. --- Nucleophilic reactions --- p.3 / Chapter I.2.3. --- Cycloaddition reactions --- p.5 / Chapter I.2.4. --- Oxidation reactions --- p.7 / Chapter I.2.5. --- Reduction reactions --- p.9 / Chapter I.3 --- New Progress in the Synthesis of Polysubstituted Furans --- p.10 / Chapter I.3.1. --- From carbohydrates --- p.11 / Chapter I.3.2. --- The Passerini-type reaction --- p.11 / Chapter I.3.3. --- "Via γ,δ-unsaturated-β-ketoesters" --- p.12 / Chapter I.3.4. --- Via tantalum-alkyne complex --- p.13 / Chapter I.3.5. --- Via addition of carbenoids --- p.14 / Chapter I.3.6. --- Via cycloaddition of alkyne and isomunchnone --- p.15 / Chapter I.3.7. --- Via reaction of metal carbene complexes with alkynes --- p.17 / Chapter I.3.8. --- Via η2-thiophosphinito complexes of cobalt --- p.18 / Chapter I.3.9. --- Via palladium-catalyzed annelation --- p.19 / Chapter I.3.10. --- "Via α,β- and β,γ-unsaturated ketones" --- p.24 / Chapter I.3.11. --- Via allenes --- p.26 / Chapter I.3.12. --- "Via 2,5-dihydrofurans" --- p.28 / Chapter I.3.13. --- Via radical cyclization --- p.28 / Chapter Chapter II. --- "The Synthesis and Applications of 3,4-Disubstituted Furans" / Chapter II. 1. --- Introduction --- p.30 / Chapter II.2. --- "Synthesis of 3,4-Disubstituted Furans" --- p.30 / Chapter II.2.1. --- Via Diels-Alder/retro-Diels-Alder reaction --- p.30 / Chapter II.2.2. --- "Via 2-butyne-l,4-diol" --- p.31 / Chapter II.2.3. --- Via ylides --- p.31 / Chapter II.2.4. --- "Via 3,4-dimethylsulpholene" --- p.32 / Chapter II.2.5. --- Via functionalized furan ring --- p.33 / Chapter II.2.5.1. --- Via Diels-Alder/retro-Diels-Alder reaction --- p.33 / Chapter II.2.5.2. --- Via furan matathesis --- p.33 / Chapter II.2.5.3. --- Via allene --- p.34 / Chapter II.2.5.4. --- "Via 3,4-disubstituted furans" --- p.35 / Chapter II.2.5.5. --- Via 3-hydroxymethylfuran --- p.36 / Chapter II.3. --- "Some Synthetic Applications of 3,4-Disubstituted Furans" --- p.37 / Chapter II.3.1. --- "Furan-3,4-dicarboxylic acid and its ester" --- p.37 / Chapter II.3.2. --- "3,4-Alkoxyfuran" --- p.39 / Chapter II.3.3. --- "3,4-Dichloromethylfuran" --- p.41 / Chapter II.3.4. --- 4-(Trimethylsilylacetylenyl)-3-(trimethylsilyl)furan --- p.42 / Chapter II.3.5. --- "3,4-Dimethylfuran" --- p.43 / Chapter Chapter III. --- Results and Discussion / Chapter III.1. --- Aim of the Present Work --- p.45 / Chapter III.2. --- ipso-Effect of Silyl Groups --- p.45 / Chapter III.3. --- "Synthesis of 3,4-Bis(trimethylsilyl)furan (105) and Its Modification" --- p.47 / Chapter III.4. --- "Acid-catalyzed Rearrangement of 3,4-Bis(trimethylsilyl)furan (105)" --- p.48 / Chapter III.5. --- "Diels-Alder Reactions of 3,4-Bis(trimethylsilyl)furan (105)" --- p.51 / Chapter III.6. --- "Acylation Reaction of 3,4-Bis(trimethylsilyl)furan (105)" --- p.54 / Chapter III.7. --- "Iodination of 3,4-Bis(trimethylsilyl)furan (105)" --- p.56 / Chapter III.8. --- Synthesis of 4-Substituted-3-(trimethylsiIyl)furan from Palladium- and Nickel-Catalyzed Cross-Coupling Reaction of 4-Iodo-3-(trimethylsilyl)furan (120) --- p.57 / Chapter III.8.1. --- Introduction --- p.57 / Chapter III.8.2. --- Heck-type reaction of 4-iodo-3-(trimethylsilyl)furan (120) --- p.59 / Chapter III.8.2.1. --- General feature of Heck reaction --- p.59 / Chapter III.8.2.2. --- Palladium-catalyzed cross-coupling of 4-iodo-3- (trimethylsilyl)furan (120) with terminal alkenes --- p.61 / Chapter III.8.2.3. --- Mechanism of result --- p.62 / Chapter III.8.2.4. --- "Synthesis of 3-(trimethylsilyl)-5,6- bis(ethoxycarbonyl)benzo[2.3-b]furan (126) from Heck- type reaction of 4-iodo-3-(trimethylsilyl)furan (120) and ethyl acrylate" --- p.63 / Chapter III.8.3. --- Stille-type reaction of 4-iodo-3-(trimethylsilyl)furan (120) --- p.66 / Chapter III.8.3.1. --- General feature of Palladium-catalyzed cross-coupling of aryl or vinyl halides with terminal alkynes (Stille-type reaction) --- p.66 / Chapter III.8.3.2. --- Palladium-catalyzed substitution of terminal alkynes with 4-iodo-3-(trimethylsilyl)furan (120): a convenient synthesis of 4-alkynyl-3-(trimethylsilyl)furan (127) --- p.67 / Chapter III.8.3.3. --- Mechanism --- p.69 / Chapter III.8.4 --- Palladium-catalyzed cross-coupling reaction of organoboronic acid with 4-iodo-3-(trimethylsilyl)furan (120) (Suzuki-type reaction) --- p.70 / Chapter III.8.4.1. --- General feature of Suzuki reaction --- p.70 / Chapter III.8.4.2. --- Suzuki-type reaction of 4-iodo-3-(trimethylsilyl)- furan (120) --- p.72 / Chapter III.8.5. --- Palladium- or nickel-catalyzed cross-coupling reaction of 4-iodo-3- (trimethylsilyl)furan (120) with bis(p-methoxycarbonyl)zinc and Grignard reagents --- p.73 / Chapter III.8.5.1. --- Palladium-catalyzed coupling of 4-iodo-3- (trimethylsilyl)furan (120) with bis(p- methoxycarbonyl)zinc --- p.73 / Chapter III.8.5.2. --- Nickel-catalyzed coupling of 4-iodo-3- (trimethylsilyl)furan (120) with Grignard reagents --- p.74 / Chapter III.9. --- "Regiospecific Conversion of 3,4-Bis(trimethyIsilyl)furan (105) to 3,4- Disubstituted Furans (147): A Novel Suzuki-Type Cross-Coupling of Boroxines" --- p.77 / Chapter III.9.1. --- General survey of boroxines --- p.77 / Chapter III.9.1.1. --- Introduction --- p.77 / Chapter III.9.1.2. --- Syntheses of boroxines --- p.78 / Chapter III.9.1.2.1. --- From boronic acid --- p.78 / Chapter III.9.1.2.2. --- From organolithium compounds --- p.78 / Chapter III.9.1.2.3. --- From trialkylborane --- p.79 / Chapter III.9.1.2.4. --- From trimethylborane and boric oxide --- p.80 / Chapter III.9.1.2.5. --- From dichloroborane --- p.81 / Chapter III.9.1.2.6. --- From carboxylic acid --- p.81 / Chapter III.9.1.3. --- The reactions of boroxines --- p.82 / Chapter III.9.1.3.1. --- Oxidation --- p.82 / Chapter III.9.1.3.2. --- Hydrolysis --- p.83 / Chapter III.9.1.3.3. --- Formation of complexes --- p.83 / Chapter III.9.1.3.4. --- Preparation of oxazaborolidine using trimethylboroxine --- p.85 / Chapter III.9.1.4. --- The structural feature of boroxines --- p.85 / Chapter III.9.2. --- Preparation and structural feature of tris[4-(trimethylsilyl)furan-3- yl]boroxine (144) --- p.87 / Chapter III.9.3. --- Palladium-catalyzed Suzuki-type cross-coupling reaction of tris[4- (trimethylsilyl)furan-3-yl]boroxine (144) --- p.89 / Chapter III.9.4. --- "Preparation and palladium-catalyzed Suzuki-type cross-coupling reactions of tris[4-(substituted)furan-3-yl]boroxines (145): Regiospecific synthesis of unsymmetrical 3,4-disubstituted furans (147)" --- p.93 / Chapter III.9.5. --- Mechanism of palladium-catalyzed Suzuki-type cross-coupling of boroxines --- p.98 / Chapter III.9.6. --- Iodination of boroxines --- p.99 / Chapter III. 10. --- "Regiospecific Synthesis of Furan-3,4-diyl Oligomers via Palladium- Catalyzed Self-Coupling of Boroxines" --- p.102 / Chapter III. 10.1. --- Palladium-catalyzed reactions of boroxines with ortho- bis(bromomethyl)arenes --- p.102 / Chapter III. 10.2. --- Reaction mechanism --- p.104 / Chapter III. 10.3. --- "Synthesis of furan-3,4-diyl oligomers" --- p.110 / Chapter III. 11. --- Conclusion --- p.116 / Experimental --- p.117 / References --- p.158 / Appendices / Chapter I. --- List of crystallographic data of tris[4-(trimethylsilyl)furan-3-yl]boroxine (144) --- p.172 / Chapter II. --- List of spectra --- p.177

Chan Siu Hin. / "June 2005." / Thesis (Ph.D.)--Chinese University of Hong Kong, 2005. / Includes bibliographical references (p. 155-195). / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstract in English and Chinese.

by Ming-Keung Wong. / Submission year appears as 1996. Graduation year on spine miss printed as 1996. / Thesis (M.Phil.)--Chinese University of Hong Kong, 1997. / Includes bibliographical references (leaves 75-78). / Acknowledgements --- p.i / Contents --- p.ii / Abstract --- p.v / List of abbreviations --- p.vi / Chapter I. --- Introduction --- p.1 / Chapter I.1 --- Reactions of furan --- p.2 / Chapter I.1.a. --- Electrophilic substitution --- p.2 / Chapter I.1.b. --- Lithiation and alkylation --- p.2 / Chapter I.2. --- Syntheses of furans --- p.3 / Chapter I.3. --- "Syntheses of 2,3-disubstituted furans" --- p.3 / Chapter I.3.a. --- Through C3-substituent-directed lithiation --- p.4 / Chapter I.3.b. --- By molybdenum pentacarbonyl-catalyzed cyclization --- p.5 / Chapter I.3.c. --- By Ag(I) catalyzed cyclization --- p.6 / Chapter I.4. --- Syntheses of rosefuran --- p.6 / Chapter I.4.a. --- Via 2-lithio-3-methylfuran --- p.7 / Chapter I.4.b. --- By Claisen rearrangement --- p.7 / Chapter I.4.c. --- By oxidative decarboxylation with lead tetraacetate --- p.8 / Chapter I.4.d. --- By prenylation of 3-methylbut-2-enolide --- p.8 / Chapter I.4.e. --- Via 3-bromo-2-furylithium --- p.9 / Chapter I.4.f. --- By reaction of α-oxo ketone dithioacetal with dimethylsulfonium methylide --- p.10 / Chapter I.4.g. --- Via allyl alcohol --- p.11 / Chapter I.4.h. --- Via γ-keto aldehyde --- p.11 / Chapter I.4.i. --- By the transformation of 5-oxogeraniol --- p.12 / Chapter I.4.j. --- By base-catalyzed cyclization of alkynoate --- p.13 / Chapter I.4.k. --- Via 3-hydroxyketone cyclization --- p.14 / Chapter I.4.L. --- By [3+2] nitrile oxide cycloaddition --- p.15 / Chapter I.5. --- "Syntheses of 2,4-disubstituted furans" --- p.16 / Chapter I.5.a. --- By electrochemical method --- p.17 / Chapter I.5.b. --- From acyclic reagents --- p.18 / Chapter I.5.c. --- "From 2,3-disubstituted furan" --- p.19 / Chapter I.5.d. --- From p-hydroxy sulfones --- p.20 / Chapter I.6. --- "Syntheses of 2,3,4-trisubstituted furans" --- p.21 / Chapter I.6.a. --- Via tantalum-alkyne complexes --- p.22 / Chapter I.6.b. --- Via intramolecular Diels-Alder reaction of oxazole alcohols --- p.23 / Chapter I.6.c. --- By using unsaturated sulfoxides --- p.24 / Chapter I.7. --- "Syntheses of 2,3,5-trisubstituted furans" --- p.26 / Chapter I.7.a. --- "From α,β-unsaturated ketone" --- p.26 / Chapter I.7.b. --- By palladium catalyzed cyclization --- p.27 / Chapter I.7.c. --- Via base-catalyzed isomerization of alkynyloxiranes --- p.28 / Chapter II. --- Results and Discussion --- p.30 / Chapter II.1 --- "Regiospecific synthesis of 2,3-disubstituted furans" --- p.30 / Chapter II. 1.a. --- "Synthesis of 2,4-bis(trimethylsilyl)furan (137)" --- p.30 / Chapter II.1.b. --- Synthesis of 2-n-hexyl-3-trimethylsilylfuran (140) and 2-benzyl-3-trimethylsilylfuran (143) --- p.35 / Chapter II.1.e. --- "Synthesis of 3-benzyl-2-N-hexylfuran (145) and 2-benzyl-3-[3,4-(methylenedioxy)]benzylfuran (153)" --- p.36 / Chapter II.2. --- Syntheses of rosefuran (4) --- p.40 / Chapter II.2.a. --- "Synthesis of rosefuran (4) from 2,4-bis(trimethylsilyl)furan (137)" --- p.40 / Chapter II.2.b. --- Synthesis of rosefuran (4) from -methyl-4-trimethylsilylfuran (158) --- p.42 / Chapter II.3. --- "Regiospecific synthesis of 2,4-disubstituted furans" --- p.44 / Chapter II.3.a. --- Synthesis of 3-trimethylsilylfuran (163) --- p.44 / Chapter II.3.b. --- Synthesis of tri(2-benzylfuran-4-yl)boroxine (165) --- p.45 / Chapter II.3.C. --- Synthesis of 2-benzyl-4-(p-tolyl)furan (166) and 2-benzyl-4-(trans-2-phenylvinyl)furan (167) --- p.46 / Chapter IL3.d. --- Synthesis of 2-benzyl-4-(trimethylsilylethynyl)furan (169) --- p.47 / Chapter IL3.e. --- "Synthesis of 2,2'-bis(benzyl)-4,4'-bifuran (174)" --- p.50 / Chapter II.4. --- "Regiospecific synthesis of 2,3,4-trisubstituted furan" --- p.51 / Chapter II.5. --- "Regiospecific synthesis of 2,3,5-trisubstituted furan" --- p.53 / Chapter III. --- Conclusion --- p.56 / Chapter IV. --- Experimental Section --- p.57 / Chapter V. --- References --- p.75 / Chapter VI. --- List of spectra --- p.79 / Chapter VII. --- Spectra --- p.81

Part I describes an investigation of the following electrophilic substitution reactions of 3-methylfuran. Acylation under Friedel-Crafts conditions yielded 3-methyl-2-acetylfuran (8) and 3-methyl-5-acetylfuran (9) in the ratio 65:35. Vilsmeier and Gatterman formylation procedures yielded 3-methylfurfural (10) and 3-methyl-5-furfural (11) in the same ratio, 93.5:6.5. Mercuration of 3-methylfuran yielded only the 2-mercuro derivative. Part II describes the isolation and structural elucidation of two major oxygen heterocyclic compounds C and D occurring in the leaves of Zeyhera tuberculosa Bur. et Verlot (Bignoniaceae). Compound C is assigned the structure 5,6,7,8-tetramethoxyflavone (25) on the basis of spectroscopic evidence. Compound D is shown to possess the structure 5,6,7-trimethoxyflavone (35). In this latter instance spectroscopic and chemical evidence could be obtained in support of the structural assignment. In particular, alkaline hydrolysis of D yielded 2,3,4-trimethoxy-6-hydroxyacetophenone (34), the identity of which was established by an unambiguous synthesis. In the synthesis of the acetophenone derivative (34), the key intermediate is 2,6-dimethoxyhydroquinone diacetate (31) which was subjected to Fries rearrangement conditions, followed by acid hydrolysis, to give 2,4-dimethoxy-3,6-dihydroxyacetophenone (33). Partial methylation of (33) yielded (34). / Science, Faculty of / Chemistry, Department of / Graduate

No description available.

No description available.

by Chun-yip Leung. / Thesis (M.Phil.)--Chinese University of Hong Kong, 1993. / Includes bibliographical references (leaves 72-76). / Acknowledgements --- p.1 / Chapter Part 1). --- The Chemistry of A Planar Cyclooctatetraene Derivatives Fused to Phenanthrene Ring --- p.2 / Chapter (I). --- Abstract --- p.2 / Chapter (II). --- Introduction --- p.3 / Chapter (III). --- Results and Discussion --- p.9 / Chapter (IV). --- Conclusion --- p.18 / Chapter (V). --- Experimental Section --- p.19 / Chapter Part 2). --- "Regiospecific Synthesis of 2,3-Disubstituted and 2,3,5-Trisubstituted Furans from 2,4-Bis(trimethyl- silyl)furan" --- p.28 / Chapter (I). --- Abstract --- p.28 / Chapter (II). --- Introduction --- p.29 / Chapter (A). --- Reactions of Furan --- p.29 / Chapter (1). --- Reactions with Electrophiles --- p.29 / Chapter (2). --- Reactions with Nucleophiles --- p.30 / Chapter (3). --- Cycloaddition Reactions --- p.31 / Chapter (B). --- Synthesis of Polysubstituted Furans --- p.32 / Chapter (1). --- By Ag(I)-Catalyzed Cyclization --- p.33 / Chapter (2). --- By Base-Catalyzed Isomerization of Alkynyloxiranes --- p.33 / Chapter (3). --- By Base-Catalyzed Cyclization- Isomerization of γ-Alkynyl Allylic Alcohol --- p.36 / Chapter (4). --- "By Palladium-Catalyzed Coupling of 2- Propargyl-l,3-dicarbonyl Compounds and Vinylic, Aryl Triflates or Halide" --- p.36 / Chapter (5). --- "From α,β-Unsaturated Ketones" --- p.38 / Chapter (C). --- Recent Achievement --- p.39 / Chapter (III). --- Results and Discussion --- p.44 / Chapter (A). --- "Attempted Synthesis of 2,4-Disubstituted Furans" --- p.44 / Chapter (B). --- "Synthesis of 2,3,5-Trisubstituted Furans" --- p.45 / Chapter (1). --- Synthesis of 2-benzyl-3-m-anisyl-5- p-tolyl-furan (30) --- p.45 / Chapter (2). --- Synthesis of 2-benzyl-3-trans-hexen- l-yl-5-p-tolyl-furan (31) --- p.51 / Chapter (3). --- "Synthesis of 2-(3,5-dimethyl)benzyl-3- p-methoxycarbonylbenzyl-5-hexyl- furan (32)" --- p.52 / Chapter (4). --- "Synthesis of 2-benzyl-3-[3,4-(methyl- enedioxy)]benzyl-furan (33)" --- p.57 / Chapter (IV). --- Conclusion --- p.60 / Chapter (V). --- Experimental Section --- p.61 / References --- p.7 2 / List of Spectra --- p.7 7 / Spectra --- p.7 9