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Rearrangement Studies and Novel Reactions of Organocadmium Reagents

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Rearrangement Studies and Novel Reactions of Organocadmium Reagents University of New Hampshire University of New Hampshire Scholars' Repository Doctoral Dissertations Student Scholarship Spring 1978 REARRANGEMENT STUDIES AND NOVEL REACTIONS OF ORGANOCADMIUM REAGENTS JAMES GERARD SHELNUT Follow this and additional works at: https://scholars.unh.edu/dissertation Recommended Citation SHELNUT, JAMES GERARD, "REARRANGEMENT STUDIES AND NOVEL REACTIONS OF ORGANOCADMIUM REAGENTS" (1978). Doctoral Dissertations. 1198. https://scholars.unh.edu/dissertation/1198 This Dissertation is brought to you for free and open access by the Student Scholarship at University of New Hampshire Scholars' Repository. It has been accepted for inclusion in Doctoral Dissertations by an authorized administrator of University of New Hampshire Scholars' Repository. For more information, please contact [email protected]. INFORMATION TO USERS This material was produced from a microfilm copy of the original document. While the most advanced technological means to photograph and reproduce this document have been used, the quality is heavily dependent upon the quality of the original submitted. The following explanation of techniques is provided to help you understand markings or patterns which may appear on this reproduction. 1.The sign or "target" for pages apparently lacking from the document photographed is "Missing Page(s)". If it was possible to obtain the missing page(s) or section, they are spliced into the film along with adjacent pages. This may have necessitated cutting thru an image and duplicating adjacent pages to insure you complete continuity. 2. When an image on the film is obliterated with a large round black mark, it is an indication that the photographer suspected that the copy may have moved during exposure and thus cause a blurred image. You will find a good image of the page in the adjacent frame. 3. 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University Microfilms International 300 North Zeeb Road Ann Arbor, Michigan 48106 USA St. John's Road, Tyler’s Green High Wycombe, Bucks, England HP10 8HR 7824554 9HELNUT, JAMES GERARD REARRANGEMENT STUDIES AND NOVEL REACTIONS Of ORGANOCADMIUM reagents , UNIVERSITY OF N£W HAMPSHIRE# PH.D.# 1978 University Microfilm s International 300 n . z e e b r o a d , a n n a r b o r , mi 48106 REARRANGEMENT STUDIES AND NOVEL REACTIONS OF ORGANOCADMIUM REAGENTS by JAMES G. SHELNUT B.A., University of Massachusetts at Boston, 1974 A DISSERTATION Submitted to the University of New Hampshire In Partial Fulfillm ent of The Requirements for the Degree of Doctor of Philosophy Graduate School Department of Chemistry May, 1978 This thesis has been examined and approved. Thesis director, Paui R. Jones Professor of Chemistry 0 A ! m J./JohnUebel Professor of Chemistry — k K Kenneth K. Andersen Professor of Chemistry Frank L. Pilar Professor of Chemistry Thomas G. Pistole Assistant Professor of Microbiology Date' ACKNOWLEDGMENT The most heartfelt appreciation is due Dr. Paul R. Jones whose enthusiasm for chemistry is only outweighed by his immense patience and warm understanding. The author also would like to thank his professors, Drs. Andersen, Uebel» Morrison and P ila r, for teaching him the wonders of chemistry. Also, the author acknowledges the financial support in the form of teaching assistantships and a summer fellowship provided by the University of New Hampshire. Special thanks go to Mr. David Urann for his technical assistance in the cyanate project; Miss Catherine Tripp for her help in the preparation of some starting materials; and Mr. James Lagana for some infrared analyses. A grant in support of original research, awarded by the Central University Research Fund, is here gratefully acknowledged. This thesis is dedicated to the only real woman, Doris, and to Superkid, Adam. TABLE OF CONTENTS PARTI AN INVESTIGATION INTO AN AROMATIC ORGANOCADMIUM REARRANGEMENT LIST OF TABLES...........................................................................................ix ABSTRACT........................................................................................................ xi INTRODUCTION .......................................................................................... 1 HISTORICAL ............................................................................................... 6 EXPERIMENTAL .......................................................................................... 57 m-Bromonitrobenzene ........................................................... 58 m-Bromoaniline .................................................................... 59 m-Bromo-NjN-dimethylaniline .......................................... 60 m-Bromofluorobenzene ...................................................... 60 m-Bromotrifluoromethylbenzene ...........................................62 Ethyl Potassium X a n th a te ................................................... 62 Ethyl m-Bromophenyl X a n th a te ...........................................63 m-Bromothiophenol ............................................................... 64 m-Bromophenyl Methyl Sulfide ...................................... 64 £,jD'-Bi a n isyl............................................................................. 65 Phenyl Cyanate .................................................................... 65 Diacetyl S u lfid e .................................................................... 66 Titration of ii-Butyllithium ............................................... 66 Acetylation of Anisole with Magnesium Chloride and Cadmium Chloride as Lewis Acids: A Control Experiment ...................................................... 66 General Procedure for Organocadmium Reactions , . 67 Standardization and Analysis of m- and £- Methoxyacetophenones by Gas Chromatography . 68 The Reaction of m-Dianisylcadmium with Acetyl C h l o r i d e ..................................................................................70 The Reaction of m-Dianisylcadmium with Acetyl Brom ide ...................................................................................... 71 The Reaction of m-Di anisyl cadmium with Acetic A nhydride ..................................................................................72 v The Reaction of m-Dianisylcadmium with Diacetyl S u lfid e..................................................................72 The Reaction of m-Di anisyl cadmium with Acetyl Chloride after the Precipitation of Magnesium Salts with Dioxane................................................ 73 The Reaction of m-Anisylcadmium Chloride with Acetyl Chloride...................................................... 74 The Reaction of m-Anisyl cadmium Bromide with Acetyl Chloride...................................................... 74 The Reaction of m-Anisyl cadmium Bromide with Acetyl Bromide...................................................... 74 The Reaction of m-Anisyl cadmium Iodide with Acetyl Chloride...................................................... 75 The Reaction of Bromine with Anisole, with and without Cadmium Chloride and/or Magnesium Chloride: A Control Experiment............................ 75 The Reaction of m-D1 anisyl cadmium with Bromine . 76 The Reaction of o-Dianisylcadmium with Acetyl C h lo rid e...............................................................78 The Reaction of m-Ditolylcadmium with Acetyl C h lo rid e...............................................................79 The Reaction of di-m-Fluorophenylcadmium with Acetyl Chloride...................................................... 79 The Reaction of di-m-Trifluoromethyl phenyl cadmium with Acetyl Chloride.............................................80 The Reaction of di-m-Methy 1 thiophenylcadmium with Acetyl Chloride...................................................... 81 jo-Deuterioanisole...................................................... 82 DC1/D?0 Quenching of .the m-Di anisyl cadmi um-Acetyl Chloride Adduct...................................................... 82 Deuterium Exchange in m- and £-Methoxyacetophenone. 83 Deuterium Exchange in m-Bromoanisole: Preparation of 2,4,6-Trideuterio-3-Bromoanisole.......................83 The Reaction of l-Methoxy-2,4,6-trideuter1o-3- phenylcadmium Reagent with Acetyl Chloride . 84 The Attempted Preparation of m-N,N-dimethylami no­ phenyl cadmium Reagent and Its Reaction with Acetyl Chloride A. Normal Methods..............................................84 B. Sodium Naphthalide Method.......................... 85 C. Active Magnesium Method.............................85 D. Lithium-Halogen Exchange............................. 86 The Reaction of m-D1 anisyl cadmium with Phenyl Cyanate..................................................................88
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