Synthesis of macrocyclic 1,3-diketones from metacyclophanes and their applications in organic synthesis.

by Siu-leung Ng.Thesis (M.Phil.)--Chinese University of Hong Kong, 1994.Includes bibliographical references (leaves 61-62).Acknowledgments --- p.iContent --- p.iiList of Schemes --- p.iiiList of Tables --- p.ivList of Spectra --- p.vAbstract --- p.viiiAbbreviations --- p.xChapter I. --- Introduction --- p.1Chapter II. --- Literature surveyChapter II.1. --- Ring expansion of cyclic enamines via a [2+2]cycloaddition --- p.4Chapter II.2. --- The Ito-Saegusa protocol --- p.6Chapter II.3. --- "The Suzuki-Watanabe-Noyori palladium(0)-catalyzed ring opening of cyclic α,β-epoxy ketones" --- p.7Chapter III. --- Synthetic plan --- p.9Chapter IV. --- Results and discussionChapter IV. 1. --- General routes to [n]metacyclophanes (24) and (n+2)- methoxy[n]metacyclophane 35 --- p.15Chapter IV.2. --- Birch reduction of 24 and 35 and ozonolvsis of 25 and 36 --- p.17Chapter IV.3. --- Synthetic applicationsChapter IV.3.1. --- Synthesis of heterocyclophanes --- p.27Chapter IV.3.2. --- Synthesis of exaltone (8) --- p.28Chapter V. --- Conclusion --- p.30Chapter VI. --- Experimental --- p.31Chapter VII. --- References --- p.61Chapter VIII. --- 1H and 13C NMR spectra of selected compounds --- p.6