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Bromine Addition to Cyclohexene in Dichloromethane ; Thorpe's Synthesis of the Caged Acid, 4-Methyltricyclo[1.1.0.0[Superscript 2-4]] Butane-1,2,3-Tricarboxylic Acid

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Bromine Addition to Cyclohexene in Dichloromethane ; Thorpe's Synthesis of the Caged Acid, 4-Methyltricyclo[1.1.0.0[Superscript 2-4]] Butane-1,2,3-Tricarboxylic Acid Brigham Young University BYU ScholarsArchive Theses and Dissertations 1962-08-02 Sulfonation of chlorobenzene and the selectivity relation ; Bromine addition to cyclohexene in dichloromethane ; Thorpe's synthesis of the caged acid, 4-methyltricyclo[1.1.0.0[superscript 2-4]] butane-1,2,3-tricarboxylic 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., "Sulfonation of chlorobenzene and the selectivity relation ; Bromine addition to cyclohexene in dichloromethane ; Thorpe's synthesis of the caged acid, 4-methyltricyclo[1.1.0.0[superscript 2-4]] butane-1,2,3-tricarboxylic acid" (1962). Theses and Dissertations. 8218. https://scholarsarchive.byu.edu/etd/8218 This Dissertation 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]. &p ~·'. - ....., (,022- -,~ :--..._ .EJg,/ SULFONA!TlON -OF OROBENZENE AND 11(_;2,; ~ THE SELECTIVITY RE · 5tION '----.-. ~- "" BROMINE ADDITION TO CYCLOHEXENE :. IN DICHLOROMETHANE THORPE'S SYNTHESIS OF THE CAGED ACID, 4-METHYLTRICYCLO [1. 1. 0. 0 2- 4] BUTANE- ' 1, 2, 3-TRICARBOXYLIC ACID A Dissertation Submitted to the Department t>f Chemistry Brigham Young University Provo, Utah In Partial Fulfillment of the Requirements for the Degree Doctor of ~hilosophy in Organic Chemistry by John A. Gurney August, 1962 -ii- This dissertation is accepted in its present'. form 1}Dythe Department of Chemistry of the Brigham Young University as satisfying the dissertation requirement for the degree of Doctor of ~hilosophy. -iii- To the Faculty and Staff of the Chemhtry Department who have dediciate:d thehi efforts to the building of a gi'flat Graduate Schbol of Chemistry. -iv- AqKNOW LEDGM~NT S Dr. Nelson has allowed much freedom of thought and action, given wise counsel and provided a stimulating working atmosphere. I am especially pleased with this training. I take deep pride in acknowledging the part n:iy;. a,ble ·wifei · who was under seige from the younger members of our family during the hours of compilation and pro'ofin~, has played in supporting and encouraging my E;fforts. We extend gratitude to our parents for assistance during many important moments. The study of bromine addition was generously supported through two research grants (NSF grant numbers G-5414 and G-14435) from the National Science Foundation. Thorpe 1s synthesis was kindly supported through part of one summer by Brigham Young University. I am grate- ful for this financial help. Brigham Young University has provided much in the way of excellent equipment, fine facilities and good supplies. I particularly appreciate the fine environment of the University. -v- TABLE OF CONTENTS Page Acknowledgements iv List of Tables viii List of Figures xii Manuscripts for the Journal of the American Chemical Society xiv THE SULFONATION OF CHLOROBENZENE AND THE SELECTIVITY RELATION Part I Introduction 1 Background 6 Results and Discussion 7 Isomer Dist.ribution 7 Competitive Sulfonation 11 Experimental Section 19 :Preparation of Sodiuµi o-, m - and p-Chlorobenzene sulfonatilJ 19 i - Isomer Distribution 21 !:>reparation of Ferric·~ .. , m - and p-Toluenesulfonates 27 Oprnpetitive Sulfonation 29 Appendix 1,Derivation Check of Ingold• s Equation 38 Appendix 2, Calculation of the Chlorobenzene • B~nzene Rate ~-s:tan:t Ratio 39 Bibliography 42 BROMINE ADDITION TO CYCLOHEXENE IN DICHLOROMETHANE Part. II Sur.vey of Basic Concepts . 47 -vi- Page Current Mechanistic Idea,s 47 Literature Background 54 Kinetics 54 Cis Addition 57 Oxygen and Light 58 . Structural and Medium Effects • 59 Discussion of Results 64 Second-Order Addition • 65 , Zero-order Addition 67 Oxygen Photo Effect 73 · Experimental Section 76 Purification of Dichloromethane, Bromine and Cyclohexene 76 Rate· Study of Cyclobe-JEEme aruLBromine in Dichloromethane 80 . Results 85 Oxygen. Photo Effect • 89 Appendix • 91 Bibliography • . 93 THORPE'S SYNTHESIS OF THE CAG5_D f,-CID, 4-METHYLTRICYCLO[ 1. 1. O. 0 - ] - BUTANE-I, 2, 3-TRICARBOXYLIC ACID Part Ill Introduction • 104 Background • 105 Discussion . 109 Ethyl Isodehydracetate • 109 , Ethyl(.3-Methylglutaconate 110 Michael Addition 115 -vii- Page 1, 1, l-Ethanetriacetic Acid . 115 1, 1, 1-Ethane-triace{yl Bromide 116 11 o(, ol', d- -TriMome-l, 1, 1-Ethanetriacetyl Bromide . 116 , . Experimental Section 118 Ethyl Isodehydracetate . 118 Absolute Ethanol 124 Diethyl {3-Methylglutaconate • • 124 Diethyl d.-Cyano-1, 1, 1-Ethanetriacetate (Michael Addition) • • 131 1, 1, 1-Ethanetriacetic Acid 132 Recrystallization Experiments with 1, 1, 1-Ethanetriacetic Acid 134 1, 1, 1-Ethanetriacetyl Bromide 135 Ethyl ol, ol 1, cJ." -Tribromo•l, 1, 1-Ethanetriacetate 137 Infrared Spectra 139 Bibliography • • 145 Abstract 1 -viii ... LIST OF TABLES Table Page 1 Comparison of the Calculated Substituent Factors (o-+) of Toiuene and the Halobenzenes 4 2 Available Isomer Distribution Data of Halobenzene Sulfonation 6 3 Melting Points of S- Benzylisothiouronium 2.,-, ~ and p-Chlorobenzene- and g•Toh,1enesulfonates 8, 21 4 Isomer Distribution Recount Data for the Sulfonation of Chlorobenzene 9, 25 5 Available Isomer Distribution Data of the Sulfonation of Chlorobenzene 10 6 Hydrolysis of 2_•, ~- and p•Chlorobe;nzen@Sulfonic Acids • 11 7 The Effect of Temperature on the Yield of Ferric m -Toluenesulfinate 12 8 Competitive Sulfonation Recount Data of Toluene and Chloro benzene 14, 34 9 Isomer Distribution and Purification Data of Sodium 'O- Chlorobenzene sulfonate-s 35. 23 10 Isomer Distribution and Purification Data of Sodium m - Cblorobenzene sulfonate .. 535. 24 11 Isomer Distributicm and Purification Data of Sodium p- Chlorobenz•ene sulfonate-s35. - 25 12 Comparison of Etllpirica.1 and Experimental Counting. Deviations • 26 13 The Isomer Distribution of the Sulfonation of Chloro- benzene • 27 14 Temperature Effect on the Yield of Ferric m -Toluene- sulfonate • 29 15 Sodium,p-ToJ.uenesulfonate-s 35 Competitive and Purifkation Data • • 31 -ix- Table Page 35 16 - Sodium p-Chlorobenzenesulfonate-s Competitive and Purification .Count Data • 32 17 Constants Used in Calculation of Partial Rate Factors • • 39 18 Comparison of Basicity and the Rate Constants of Hydrogen Chloride -and Chlorine Addition • 52 19 'Surface Catalysis of Bromine.-Ethylene Addition .56 2.0 -Effect" of Structure on Bromine Addition 63 2.1 Classes of Bromine Addition, Reactions 64 22 -Promotion of Bromine Addition to -Cyclohexene by Light • • • • 65, 81 23 Bromine Addition to Cyclohexene 65 24 Inhibition of Bromine Addition to Cyclohexene by Hydro- gen Bromide. Cyclohexene ·Distilled frorrLSodium . 66, 86 25 Inhibition of Bromine Addition to Cyclohexene by Hydro- gen Bromide. Cyclohexene from a Cuprous Chloride Adduct • • • • • • 66, 87 26 Bromine Addition to Cyclohexene Purified through a . Copper ·(I) Chloride Adduct •. Zero-Order • 67 27 _Re-activity of Various Brominating Re-agents with Allyl- trimethylammonium ,Perchlorate • • 72 28 Description of the Aurora Borealis - . 74 30 Procedure for Determination of Bromine-Cyclohexene Re-action Rates • • • • 83 31 Bromine Addition to Cyclohexene Distilled from.Sodium 86 32 Bromine Addition to Cyclohexene, Least Hydrogen Bromide Present (A) • • • 88 33 Bromine Addition to Cyclohexene, Some Hydrogen Bromide Present (B) • • • 88 ~x- Table Page 34 Bromine Addition to Cyclohexene, Much Hydrogen Bromide Pre sent (C) 88 35 Bromine Addition to Cyclohexene, Most Hydrogen Bromide Present (D) .• 89 36 ·Pressure and Photo Effect Intensity 89 37 Pressure and the Repeats of the Photo Effect 90 38 Effect of Temperature on the Yield of Ethyl Isodehydracetate 109 39' The Relationship of Ethyl 13-Methylglutaconate Yield and Ethyl Isodehydracetate Storage 111 40 Ferric Chloride Test of Various Ethyl Isodehydracetate Samples and the Yield of Ethyl 13-Methylglutaconate 112 41 Effect of Distillation on the Physical Properties of Ethyl Isodehydracetate 112 42 Elemental Analysis of Various Ethyl Isodehydracetate Samples 113 43 Promotion of a.-Bromination of 1, 1, 1-Ethanetriacet~l Bromide 116 44 Ethyl Isodehydracetate Synthesis and Isolation Variables 121 45 Yields and Physical Constants of Ethyl Isodehydracetate • 122 46 Ferric Chlo,ride Test of Various EIDA Samples . 122 Effect of Redistillation on Physical Properties of Ethyl Isol:l.ehydracetate 123 48 Ultraviolet Spectra of Ethyl Isodehydracetate 123 49 Yields and Physical Properties of Diethyl 13.. Methyl- glutaconate 126 50 Diethyl 13--Methylglutaconate Synthesis Variables 127 51 Reagent Variation During the Synthesis of Diethyl 13-Methylglutaconate 128 -xi- Table Page 52 -Effect of Various Metals on the·Synthesis of Diethyl /3 -Methylglutaconate • 129 53 Ethyl Is odehydracetate Reaction ,Mixture Treatment and Diethyl /3 -Methylglutaconate ·Yields • • • 130 54 The Guerbet Reaction and the Yield of Diethyl (3 -Methyl- glutaconate • • • • • • 131 55 Decarboxylation of Diethyl cl-Carboxy-1, 1, l•Ethanetri- acetic ·Ester ·Nitrile, ..Michael Addition .Product 1.32 56 Extraction of 1, 1, 1-Ethanetria.cetyl Bromide Synthesis Products • • • • • 136 57 Trace Effects on ct -Br-omination of 1, l, l•Ethanetriacetyl Bromide 138 -xii- TABLE OF FIGURES Figures Page 1 Variation in~ of Para Substitution in ,Cblorobenzene, Toluene and Anisole as a. Function of P 3 2 . Comparison of the Para and Meta Partial Rate-Factors
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