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
| Identifer | oai:union.ndltd.org:cuhk.edu.hk/oai:cuhk-dr:cuhk_322587 |
| Date | January 1997 |
| Contributors | Wong, Ming-Keung., Chinese University of Hong Kong Graduate School. Division of Chemistry. |
| Source Sets | The Chinese University of Hong Kong |
| Language | English |
| Detected Language | English |
| Type | Text, bibliography |
| Format | print, vi, 108 leaves : ill. ; 30 cm. |
| Rights | Use of this resource is governed by the terms and conditions of the Creative Commons “Attribution-NonCommercial-NoDerivatives 4.0 International” License (http://creativecommons.org/licenses/by-nc-nd/4.0/) |
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