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The Reaction of Lithium Nitride with Organic Esters. James Michael Greene Louisiana State University and Agricultural & Mechanical College

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The Reaction of Lithium Nitride with Organic Esters. James Michael Greene Louisiana State University and Agricultural & Mechanical College Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1965 The Reaction of Lithium Nitride With Organic Esters. James Michael Greene Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Greene, James Michael, "The Reaction of Lithium Nitride With Organic Esters." (1965). LSU Historical Dissertations and Theses. 1011. https://digitalcommons.lsu.edu/gradschool_disstheses/1011 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. This dissertation has been Go—6408 m icrofilm ed exactly as received GREENE, James Michael, 1938- THE REACTION OF LITHIUM NITRIDE WITH ORGANIC ESTERS. Louisiana State University, Ph.D., 1965 Chemistry, organic University Microfilms, Inc., Ann Arbor, Michigan Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. THE REACTION OF LITHIUM NITRIDE WITH ORGANIC ESTERS A Dissertation Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of t-\ .o- -nu,JT^ u — i^uCuOr u - l riliiuaupuj in The Department of Chemistry by James Michael Greene BoSo> McNeese State College, 1961 January, 1965 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ACKNOWLEDGMENT The author wishes to express his sincere appreciation to Dr. Paul E. Koenig who conceived and directed this investigation. He would also like to express his gratitude to Professor James G. Traynham for his interest in the author. To his wife, Peggy, the writer wishes to express his deepest appreciation for her inspiration and assistance which made the completion of this work possible. He also wishes to thank his parents for their constant encouragement. The author gratefully acknowledges the financial support received from the National Science Foundation during this investigation. ii Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. TABLE OF CONTENTS Chapter I. INTRODUCTION. ............ ........... II. HISTORICAL .................. .................... III. DISCUSSION .............. ........... A. Theoretical Considerations. ........ B. Reactions of Esters in Various Solvents . C. Reactions Utilizing Excess Ester as Solvent D . Reaction Mechanism. ....oooe.o.o IV. EXPERIMENTAL.................... .. A. The Preparation and Purification of Esters. Bo The Reaction of Lithium Nitride with Esters in Various Solvents. ........... 1. Phenyl Benzoate in Diglyme 2. Phenyl Benzoate in Tetrahydrofuran 3. £-Propyl Benzoate in Toluene I;. _n-Propyl Benzoate in Diglyme 5. Cyclohexyl Benzoate in Decalin 6. Cyclohexyl Benzoate in Diglyme 7. Ethyl Acetate in Diglyme 8. Ethyl Acetate in Pyridine 9. n_-Propyl Formate in Pyridine 10. Methyl Benzoate in Xylene-Diglyme C. The Reaction of Lithium Nitride with Esters Using Excess Ester as Solvent ........ 1. Cyclohexyl Benzoate 2. n_-Propyl Formate 3. Ethyl Formate ij.. Ethyl Acetate 5. Isopropyl Propionate V. CONCLUSION. ......... .......... VI. A SELECTED BIBLIOGRAPHY ............ VII. VITA. ..................... iii Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. LIST OF TABLES Table Page I Table of Reactions 13 iv Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. :* LIST OF ILLUSTRATIONS Illustration Rage I Addition Funnel and Condenser 52 v Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ABSTRACT The reactions of esters with bases proceed primarily through a nucleophilic attack at the carbonyl carbon or abstraction of an alpha hydrogen to produce carbanions which undergo subsequent condensations. Lithium nitride, an extremely strong base but reportedly a weak nucleophile, has been observed to react with esters in an unexplained manuer. The purpose of this investigation was to expand the relatively limited knowledge of this reaction. The following solvents were investigated as possible systems for the reaction of lithium nitride with esters: decalin, diglyme, pyridine, tetrahydrofuran, toluene, and xylene. None of these solvents was suitable as a reaction medium. Reactions in diglyme, decalin and pyridine produced anomalous results, and no apparent reaction occurred in the other solvents. The periodic addition of small amounts of lithium nitride directly to the refluxing esters was found to be the most satisfactory procedure. The reaction appeared to proceed exclusively through nucleophilic attack by the nitride ion (or a related chemical species) on the carbonyl carbon of the ester. The products from the reactions of simple aliphatic esters with lithium nitride were neutralized with acetic acid and produced high yields of the corresponding amides and alcohols. Benzoate and formate esters reacted in an analogous manner. However lithium alkoxide produced by the cleavage, of the alkyl formates catalyzed the decomposition vi Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. of these esters to carbon monoxide and alcohol. No tertiary amides could be isolated from any of these reactions. Prom these results it is evident that the nitride ion is equal if not superior to the hydroxide ion in nucleophilic reactivity toward esters. The reaction of lithium nitride with esters is of theoretical interest but is of little practical value as a means of ester- cleavage. vii Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. INTRODUCTION Ester hydrolysis has been utilized by man in the production of soap since the earliest times. Few organic reactions have been subjected to as thorough an inves­ tigation as the esterification and hydrolysis of esters. The reversibility of these reactions involving an acid, an alcohol, an ester, and water has long been recognized. With this realization investigators have been able to obtain much information concerning one process by observing the reverse reaction. The rate of cleavage of esters is greatly enhanced by both acids and bases. Hydrolysis is often reported as being "base-catalyzed.** This terminology is not entirely correct since base is required in a stoichiometric amount and is not regenerated at any subsequent step in the process. Saponification and base-induced hydrolysis are more suitable terms for ester hydrolysis promoted by base. Numerous inorganic bases have been used to effect saponification of esters. The ionic nitrides which have previously been considered to be quite unreactive with 1,2 most organic compounds have not been investigated as possible reagents for the cleavage of esters. However, (1) F. Briegleb and A. Geuther, Ann., 123, 237 (1862). (2) M. A. Smits, Rec. trav. chira., 12, 202 (1893). 1 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Koenig and coworkers have reported that ionic nitrides, lithium nitride in particular, appear to be reactive with a number of organic compounds. Lithium nitride was selected because of its relative stability and availability. Sodium nitride and potassium k nitride decompose explosively when heated and cannot be used. Lithium nitride, at least formally, contains the nitride ion (N“^). This tri-negative ion is unique since 5 it is the only monatomic ion of its type known. Because of the size (ionic radiu.s of 1.71 A°)^ and large negative charge of the nitride ion, lithium nitride should demonstrate strong basic and nucleophilic properties. 7 In his thesis Morris reported the reaction of lithium nitride with several esters. The present investigation has been undertaken to study more fully the nature of the reaction and if possible to elucidate the mechanism by which it proceeds. (3) P. E. Koenig, J. Morris, E. Blanchard, and P. S. Mason, J. Org. Chem., 26, 14-777 (1961). (I4.) N. V. Sidgwick, The Chemical Elements and Their Compounds, Clarendon Press, Oxford, 1950, vol. I, pp. 8ip-d6 . (5) T. Moeller, Inorganic Chemistry, John Wiley and Sons, Inc., New York, N.y T, 1552, p. 57°. (6 ) E. Masdupuy, Ann. chim. (Paris), (13) 2, 527 (1957). (7) J. M. Morris, Thesis, Louisiana State University (1959), p. 10. Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. HISTORICAL Nitrides, and in particular ionic nitrides, have been virtually ignored as possible reagents in organic chemistry. The nitrides are generally divided into three classes:^ ionic, covalent ard interstitial. Ionic nitrides are derived from all group II metals except mercury and thorium and from lithium and copper (I). They are usually prepared by the direct combination of the elements. Covalent nitrides are subdivided into volatile and nonvolatile classes. The volatile covalent nitrides are derived from non-metallic elements such as hydrogen and carbon. The nonvolatile ones are formed from group III metals and exist as large molecules having structures similar to diamond or- graphite. They are hard and quite unreactive. Interstitial nitrides are derived from
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