Affordable Access

A radical pathway for reductive dehalogenation and nucleophilic substitution of hetaryl halides

  • Halides ( Lcsh )
  • Reduction (Chemistry) ( Lcsh )
  • Chemistry Thesis Ph. D
  • Dissertations
  • Academic -- Chemistry


Radical pathway for reductive dehalogenation and nucleophilic substitution of hetaryl halides. A RADICAL PATHWAY FOR REDUCTIVE DEHALOGENATION AND NUCLEOPHILIC SUBSTITUTION OF HETARYL HALIDES By TERENCE MILLER OESTREICH A DISSERTATION PRESENTED TO THE GRADUATE COUNCIL OF THE UNIVERSITY OF FLORIDA IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY UNIVERSITY OF FLORIDA 1973 To My Wife, Martha ACKNOWLEDGEMENT The author will always be indebted to Dr. John A. Zoltewicz, Chairman of his Supervisory Committee, for his perceptive guidance and patient support during the course of this research. Appreciation is also extended to the other members of his Committee: Dr. Merle A. Battiste, Dr. Richard D. Dresdner, Dr. Paul Tarrant, and Dr. Robert B. Bennett. Special gratitude is due his wife, Martha, for her unfailing support and understanding during the disap- pointments and achievements of these years. The friendship and assistance of other members of his research group will always be remembered. Thanks are extended to his wife, Martha, and Mrs. Judi Nielsen for their help in preparing the manuscript, Financial support from the Chemistry Department of the University of Florida and from the National Science Foundation is gratefully acknowledged. TABLE OF CONTENTS Page ACKNOWLEDGEMENT iii LIST OF TABLES vi LIST OF FIGURES viii ABSTRACT xi CHAPTER 1 . INTRODUCTION 1 2. ALKOXIDE ION PROMOTED REDUCTIVE DEHALOGENATION OF HETARYL HAL IDES 5 Results 5 Discussion 37 3. ALKOXIDE ION PROMOTED NUCLEOPHILIC SUBSTITUTION OF HETARYL HALIDES 52 Results 52 Discussion 80 4. AMIDE ION PROMOTED NUCLEOPHILIC SUBSTITUTION OF 4-HALOISOQUINOLINES 91 Results 91 Discussion 104 5. COVALENT AMINATION AND ANIONIC SIGMA COMPLEXES OF ISOQUINOLINE DERIVATIVES 110 Results 110 Discussion 118 6. EXPERIMENTAL 123 Instrumentation 123 IV Page Chemicals 124 Preparations 125 Thin Layer Chromatogr

There are no comments yet on this publication. Be the first to share your thoughts.