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UC San Diego Electronic Theses and Dissertations UC San Diego UC San Diego Electronic Theses and Dissertations Title Development and Reactivity Studies of Highly Ambiphilic Carbenes Permalink https://escholarship.org/uc/item/57t561ss Author Weinstein, Cory Publication Date 2018 Peer reviewed|Thesis/dissertation eScholarship.org Powered by the California Digital Library University of California UNIVERSITY OF CALIFORNIA, SAN DIEGO Development and Reactivity Studies of Highly Ambiphilic Carbenes A dissertation submitted in partial satisfaction of the requirements for the degree of Doctor of Philosophy in Chemistry by Cory Michael Weinstein Committee in charge: Guy Bertrand, Chair Michael K. Gilson Joseph M. O’Connor Arnold L. Rheingold Haim Weizman 2018 Copyright Cory Michael Weinstein, 2018 All rights reserved The dissertation of Cory Michael Weinstein is approved, and it is acceptable in quality and form for publication on microfilm and electronically: Chair University of California, San Diego 2018 iii DEDICATION This dissertation is dedicated to my mom Without her endless sacrifices and unconditional love and support Nothing I have ever done would have been possible iv EPIGRAPH “luck is always better than skill at things” -James Murphy but “chance favors the prepared mind” -Louis Pasteur v TABLE OF CONTENTS Signature Page ............................................................................................................................................. iii Dedication .................................................................................................................................................... iv Epigraph ........................................................................................................................................................ v Table of Contents ......................................................................................................................................... vi List of Abbreviations ................................................................................................................................. viii List of Figures ............................................................................................................................................. xii List of Schemes ......................................................................................................................................... xvii List of Tables ............................................................................................................................................. xxi Acknowledgments ..................................................................................................................................... xxii Vita ........................................................................................................................................................... xxix Abstract of the Dissertation ..................................................................................................................... xxxi Chapter 1 : General Introduction .................................................................................................................. 1 1.1 Molecular and Electronic Description of a Carbene ...................................................................... 1 1.2 A Brief History of Carbenes ........................................................................................................... 5 1.3 Measuring the Steric, Donor, and Acceptor Properties of Carbenes ............................................ 13 1.3.1 Measuring the Sterics of Carbenes ............................................................................................ 13 1.3.2 Measuring the Donor Properties of Carbenes ........................................................................... 17 1.3.3 Measuring the Accepting Properties of Carbenes ..................................................................... 22 1.4 Supporting Info ............................................................................................................................ 27 1.5 Acknowledgements ...................................................................................................................... 29 1.6 References .................................................................................................................................... 29 Chapter 2 : Exploring the Reactivity of White Phosphorus with Electrophilic Carbenes .......................... 35 2.1 Introduction .................................................................................................................................. 35 2.1.1 Elemental Phosphorus: Production and Uses ............................................................................ 35 2.1.2 P4 Reactivity with Carbenes ...................................................................................................... 36 2.2 Synthesis of a P4 Cage, P8 Clusters and Other Carbene-P4 Reactivity Studies ............................. 42 2.3 Conclusion .................................................................................................................................... 51 2.4 Experimental ................................................................................................................................ 52 2.4.1 General Considerations ............................................................................................................. 52 2.4.2 Synthetic Procedures ................................................................................................................. 52 2.4.3 Crystallographic Data ............................................................................................................... 54 2.5 Acknowledgments ........................................................................................................................ 57 2.6 References .................................................................................................................................... 57 Chapter 3 : Cross-coupling Reactions between Stable Carbenes ................................................................ 60 3.1 Introduction .................................................................................................................................. 60 vi 3.2 Synthesis of Carbene Heterodimers and Subsequent Rearrangement Reactions ......................... 64 3.3 Computational Calculations ......................................................................................................... 70 3.4 Conclusion .................................................................................................................................... 74 3.5 Experimental ................................................................................................................................ 75 3.5.1 General Considerations ............................................................................................................. 75 3.5.2 Synthetic Procedures ................................................................................................................. 76 3.5.3 Crystallographic Data ............................................................................................................... 77 3.5.4 Computational Details .............................................................................................................. 81 3.6 Acknowledgements .................................................................................................................... 100 3.7 References .................................................................................................................................. 100 Chapter 4 : Development and Reactivity Studies of Cyclic (Alkyl)(amino)carbenes with Expanded Ring Sizes .......................................................................................................................................................... 105 4.1 Introduction ................................................................................................................................ 105 4.2 Highly Ambiphilic Room Temperature Stable Six-Membered Cyclic (Alkyl)(amino)carbenes 123 4.2.1 Synthesis ................................................................................................................................. 123 4.2.2 Quantum Mechanical, Spectroscopic, and Reactivity Studies of CAAC-6 Derivatives ......... 134 4.3 Development of All-alkyl Substituted Six-membered Cyclic(alkyl)(amino) Carbenes ............. 146 4.3.1 Synthesis ................................................................................................................................. 146 4.3.2 Coordination Complexes Featuring Monomethylated CAAC-6 Derivatives ......................... 149 4.3.3 All-alkyl CAAC-6-Selenium Adducts Reveal Novel Examples of Non-Classical Hydrogen Bonding ................................................................................................................................... 160 4.4 Conclusion .................................................................................................................................. 167 4.5 Experimental .............................................................................................................................. 167 4.5.1 General Considerations ........................................................................................................... 167 4.5.2 Synthetic Procedures ..............................................................................................................
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