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The Bromination of 1,1,1-Ethanetriacetic Acid

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The Bromination of 1,1,1-Ethanetriacetic Acid Brigham Young University BYU ScholarsArchive Theses and Dissertations 1958-07-01 The bromination of 1,1,1-Ethanetriacetic acid John A. Gurney Brigham Young University - Provo Follow this and additional works at: https://scholarsarchive.byu.edu/etd BYU ScholarsArchive Citation Gurney, John A., "The bromination of 1,1,1-Ethanetriacetic acid" (1958). Theses and Dissertations. 8217. https://scholarsarchive.byu.edu/etd/8217 This Thesis is brought to you for free and open access by BYU ScholarsArchive. It has been accepted for inclusion in Theses and Dissertations by an authorized administrator of BYU ScholarsArchive. For more information, please contact [email protected], [email protected]. TEE BROMINATIONor 1,1,1-ETHANETRIACETIC ACID An Abstract of a Thesis Submitted to the Department of Chemistry Brigham Young University- Provo, Utah In Partial Fulfillment of the Requirements for the Degree of Master of Science John A. Gurney July, 1958 ABSTRACT Essential to the entire field of Organic Chemistry is the nature of the carbon to carbon bond. Our current concepts and guiding principles concerning it are almost solely constructed from aliphatic compounds, certain simple ring species, and aroma.tic systems. Except for special cases, aliphatic and aromatic types are felt to be mildly strained or free from internal tension while the alicylic small and medium ring compounds are the so-called strained molecules. These strained compounds involve bending back or com- pression of two of the four carbon bonds from an equilibrium position. Distortions of more complex origin occur in the paracyclophanes and hexahelictne, etc. The theory considering strain of two of the four carbon bonds might well be extended to include three bonds. Simple caged compound core types testing three-bond strain. are the tetrahedron, trigonal prism <Ladenburg>, and cube. The 2 4 successf'i½ synthesis of a unique compound, 4-methyl tricyclo[1.1.o.0 - J~ butane-1,2,3-tricarboXYlic acid containing the three-bond strained tetrahedral core was repotj;ed by Beesley, Thorpe; and Ingold thirty eight years ago. With the exception of unsuccessful efforts by 'Woodward and Larson, this area of chemistry has remained virtually inactive since that time. Our reinvestigation df this remarkable synthesis,has revealed method omissions vital to acquiring the compounds leading to I. These methods, a prelimirurl-y objective of this research and apparently commonplace in the laboratory of Thorpe, particularly involved•' the pre- paration of l,l,1-ethane triacetic acid II and triethyl tribromo-1,1,1- 1 1 .. ethane triacetate, III. -3- The tri acid II was very difficult to purify by crystallizing with the techniques of frequent present-day use. Thorpe made no mention of temperature in his accounts, but obtained the acid in good condition. Our work has shown the acid can be easily purified by crystallizing from 50 j hydrochloric acid solution at 65°-70° c. This higher purity product can then be brominated with phosphowus pentabromide 1under special collditions. These are only partially stated by Thorpe. Our work has shown that III can be brominated by making phosphorus pentabromide J.11a.i:!m with slow bromine addition l, . ....__ to a mixture of I+ and phosphorus tribromide. Compoundsnecessary to the acquisition of II and III are e"1'1 isodebydracetate IV, ethyl ~-methyl glutaconate v,·andethy"l ~ . a-cyano ~,~-dimetbylpropane tricarboxylate VI <a Michael condensation product>. Discussion of the plausible reasons for method omissions, the synthesis deletions and results of greater interest, reaction achenes . J leading each compound to its successor, and the experimental details of compounds II tbrough VI are presented in the Thesis. Appended is a proposed manuscript for p~blishing in the Journal of the American Chemical Society. THEBROMINATION OF 1,1,1-ETHANETRIACETIC ACID A Thesis Submitted to the Department of Chemistry Brigham Young University Provo, Utah In Partial Fulfillment of the Requirements for the Degree of Master of Science By John A., Gurney July, 1958 This thesis by John A. Gurney is accepted in its present form by the Department of Chemistry of the Brigham Young University as sat­ isfying the thesis requirement for the degree of Master of Science. -ii- ACXNOWI:sDGEMENTS The writer grateraJ.17 acknowledges the prudent guidance and assistance ot Dr, K. LeBoi Nelson wh6 directed the labors which form the basis of this thesis. Also appreciation is gratetally extended to Ralphena, his wife who patiently and dUigently typed the manuscript, andJfor her suggestions which have been incorporated into the text. In ~ddition, the use of present Universit7 facilities have come to be cherished bf the currently developing researcher, the author. He wishes to express gratitude for the use of this fine equipment and laboratory space. Further appreciation is extended tor support from the University during part of one summer. -111- TABLEOF CONTENTS Page ACKNOWLEDGEMENTS.• • •••• ••• • • • • • • • • • • • • • iii LIST OF TABLES•• • • • • • • • • • • • • • • • • • • • • • • V LIST OF ILLUSTRATIONS.• • • • • • • • • • • • • • • • • • • • vi I. INTRODUCTION.• • • • • •• • • • • • • • • • • • • • • 1 Baeyer strain theory Simple caged-ring systems II. HISTORICALBACKGROUND. • • • • • • • • • • • • • • • • • 4 Detailed account Later labors III. OURWORK •• • • • ••••• • • • •. •. •. • • • •. 7 Ethyl isodehydracetate,VI Mich•ael condei\sation 1,1,1-ethane triacetic acid, IX Bromination of IX IV. .REACTIONSCHEMES ••• • • • • • • • • • • • • • • • • • 19 v. EXPERIMENTALDETAILS • • • • • • • • • • • • •• • ••• 26 APPENDIX••••••••• • • • • • • • • • • • • • • • • • • 51 Proposed manuscript for publishing in the Journal of the AmeriMn Chemical Society Elemental Analysis LITERATURECITED • • • • • • • • • • • • • • • • • • • • • • • 55 -iv- LIST OF TABLES Table· Page; l. Yield of Michael Condensation using Diethylmalonate. 12 2. Yield of ,f,{ichael Condensation Ethyl ~-methyl glutaconate VIII-receiving •••• ., o ••• 0 0 0 0 12 3. Synthetic Results: Ethyl isodehydracetate. e ,. 0 0 26 4. Concentrated Hydrochloric Acid-temperature, volume and generation time •••••• o • •• q. • 28-29 5. Totals of Table 4 ••••• • •••••• o • • o. • 29 6. pH and color changes of ethyl isodehydracetate, • • 32 7. Ethyl isodehydracetate elemental analysis. • • • • • 33 s. Washing and recrystallizing results •• • • • • • • • 36 9 .. Esterification distillation results •• 0 • 0 0 0 0 e 37 10. Elemental analysis of ethyl ~-methyl glutaconate • • 39 11. Distillation of neu.tral diethyl·malQnate condensation product •••••••••• • • 0 • • • 44 12. Distillation of acidic diethyl malonate condensation product •••••••••• eooeoo 45 ~ LIST OF ILLUSTRATIONS Figure Page 1. Simple caged compound types •• • • • ••• • • • 1 2. Synthesis Pathway ••••••• • • • • • • • • • 8 -vi- I. Introduction Baezer strain theor;y.-Dr. Adolf von Baeyer, at the end of the :nineteenth . century was an important force in establishing organic chemistry as the ( ,, fascinating search for ntN QQmpoundsand knowledge. <26> In 1885 he gave added force to the tetra•lent theory of Van1 t Hoff <17> with his \'Spann- ungstheorie/ This tension theory dailt with the change in stability when carbon bonds were pushed back or compressed from an equilibrium position and served as an explanation for the known ring compounds of the day. Although it has been modified in use since that time, it has continued to stimulate and impell the synthesis of many- so-called strained molecules. This deviation from the optimum angle of 109° 281 between two of the four bonds of carbon; might well be increased to.three bonds with a subsequent possible strain increase. Caged:..RingSystems.-Caged-eompound types testing three-bond strain are 4:·, practically unknown to present day chemistry, These are: the tetra- hedron, trigonal prism <Ladenburg>, and cube. However, three compound cores might be possible. I I LI ___ _ / / / / Stable. ? Unstable Weltner <35>has given theoretical consideration to the stability .. -2- of the tetrahedral and cubic systems. From his calculations, he con- cluded that the first structure with the so-called 60° adjacent angles would be stable and the c~bic form would be non-feasible. A Ladenburg type structure su.ch as Farmer pursued <9 >, may also be postulated and expected :aear the border"line between stability and non-existence. The tetrahedral. '·r system haa, been the object of our interest. Tile ultimate goal of our present e.fferts is to obtain 1,2,3,4- 'te'l.r~:tby'l tric;yclo_,lj.,l,O.O, 2~___.Jbutane, I. This remarkable stru.cture I. contahis'three kinds or bonds: two carbon types and a carbon-hydrogen bond~ The methyl-to-bridge carbon bond should be essentially normal whiie.\he bridge carbon to carbon bonds should be highly strained. Ap.d above all, the molecule presents multiple s~etry which would lend it to some interesting lDS&sure:mentspossible today, such as spect,ral study, X-ray diffraction, and nuclear Jlllgnetie reson$l'lce. There are three compounds containing this core. They are the acid II, potassit2lll salt III, ,_,,,,. C COaH '-".;e,'1,ti,,H,r C02Et ,.,;,.__ \ I C COaK . ~~0c \ I \ I ~ I \ I N\ I 11\ H02G C02H KOaC C02K Eto2C C02Et II III IV -3- and trietql ester IV of, 4-met!Qrltriqclo [!.1.0.0 ,a-~ butane-1,2,.3- trioarbo~lic acid, and are possible precursors for I. A study' of the preparation of the compoundswas begun. In their synthesis, it was necesaaey that experimental detail be observed and rediscovered clue to .apparent ..method
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