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Orientation Reactions of Phenoxathiin and Its Derivatives Scott H Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1955 Orientation reactions of phenoxathiin and its derivatives Scott H. idtE Iowa State College Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Organic Chemistry Commons Recommended Citation Eidt, Scott H., Or" ientation reactions of phenoxathiin and its derivatives " (1955). Retrospective Theses and Dissertations. 13430. https://lib.dr.iastate.edu/rtd/13430 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. NOTE TO USERS This reproduction is the best copy available. UMI I ORIENTATION REACTIONS OF PHENOXATHIIN AND ITS DERIVATIVES by Soott H. Eldt A Dissertation Submitted to the Graduate Faculty In Partial Fulfillment of The Requlrementfi for the Degree of DOCTOR OF PHILOSOPHY Major SubJejct; • .Org-aalc Chemistry Approved: Signature was redacted for privacy. In Charge of Major Work Signature was redacted for privacy. Head of Major Departmerrt Signature was redacted for privacy. htsttii ux u-x*eiuu«ive wuxlege Iowa state College 1955 UMI Number: DP12681 INFORMATION TO USERS The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleed-through, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. UMI UMI Microform DP12681 Copyright 2005 by ProQuest Information and Learning Company. All rights reserved. This microform edition is protected against unauthorized copying under Title 17, United States Code. ProQuest Information and Learning Company 300 North Zeeb Road P.O. Box 1346 Ann Arbor, Ml 48106-1346 . ; •r 11 /i • J •' TABLE OF CONTENTS Page INTRODUCTION 1 HISTORICAL 6 Nomenclature 6 Phyeloal Properties of Phenoxathlln 8 Pii^slcal Properties of Phenoxathlln-10-oxlde 14^ Physical Properties of Phenoxathlln-10->dloxlde 16 Methods of Preparation of Phenoxathlln 18 Preparation of Phenoxathlln-10-oxide 23 Preparation of Phenoxathlln-10-dloxlde 27 Ring Closure Methods of Preparation of Phenoxathlln Derivatives 28 Oxidation Reactions 52 Reduction Reactions 58 Substitution Reactlone 61 Halogenatlon reactions 61 Friedel-Crafts reactions 66 Nitration 72 Sulfonation reactions 77 Metalation reactions 82 Cleavage reactions 89 Derivatives of Phenoxathlln 92 Bibliography of Phenoxathlln 110 EXPERIMENTAL 117 Reactions Involving Metalation and Subeequent Carbonatlon 117 General procedure 117 Reaction of phenoxathlln with one equivalent of s,-hutylllthium at low temperature 119 Reaction of phenoxathlln with one equivalent of n-butyllithlum at 35® 120 R^actTon of phenoxathlln with two equivalents of n-butyllithlum 122 Tl 1043 ill Page Run I 122 Run II 125 Run III 126 Reaction of phenoxathiln with methyllithium 129 Reaction of phenoxathiln with four equivalente of n-butyllithium I30 Reaction of phenoxathiln with phenylcalcium iodide 132 Preparation of dimethyl ^,6~phenoxathiin- dioarhoxylate 133 Preparation of dimethyl 1,6-phenoxathiin- dioarboxylate 134 Esterifioation of a mixture of phenoxathiindicarboxylic acids 135 Reaction of phenoxathiin-10«oxide with n-butyllithium 136 Reaction of phenoxathiin-lO-oxide with three equivalents of |i-butyllithlum at -50® 138 Reaction of phenoxathiin-lO-oxide with two equiralente of n-butyllithium at -50 1^0 Reaction of phenoxathiin-lO-oxide with one equivalent of n-butyllithium at -50® 1^1 Reaction of phenoxathiin-lO-oxide with two equivalents of ja-butyllithium at -20®, room temperature 141 Reaction of phenoxathiin-lO-oxide with three equivalents of n-butjllithium at room temperature ~ 142 Reaction of phenoxathiin-lO-oxide with tl^ee equivalents of methyllithlmn at -20®, 0® 143 Reaction of phenoxathiin-lO-oxide with three equivalents of methyllithima at 35® 145 Reaction of phenoxathiin-lO-dioxide with two equivalents of jn-butyllithium 146 Reaction of phenoxathiin-lO-dioxide with one and one-half equivalents of |i-butyllithium 148 Reaction of phenoxathiin-lO-dioxide with one equivalent of methyllithium 150 Reaction of phenoxathiin-lO-dioxide with phenylcalcium iodide in tetrahydrofuran I5I Preparation of dimethyl 1,9-phenoxathiin- dicarboxylate 10-dioxide 152 Preparation of diethyl 1,9-phenoxathiin- dicarboxylate 10-dioxide 153 iv Page Reaction of dlphenyl ether with two equlTalente of n-butylllthliim 15^ Reaction of phenoxathlln-10-oxlde with 2,2'-dilithiodiphenyl ether 155 Reactions Involving 2-SubBtituted Phenoxathlins 158 Friedel-Crafts acetylation of phenoxathlin 158 Run I 158 Run II 159 Preparation of 2-acetylphenoxathlin oxirae 162 Preparation of 2«aalnophenoxathiin by the Beckmann rearrangement of 2-acetyl- phenoxathlin oxime 163 Preparation of 2-broffipphenoxathlin by the Sandraeyer reaction 164 Run I 16^^ Run II 165 Reactions Involving 2-Subetituted Phenoxathiin- 10-dioxides 166 Preparation of 2-nltrophenoxathiln-lO- dioxide 166 Preparation of 2-aaiinophenoxathiin-lO- dioxide by reduction of 2-nitrophenoxathiin-lO-dloxide 167 Preparation of 2-ohlorophenoxathiin-lO- dioxide by the Sandmeyer reaction 169 Preparation of 2-bromophenoxathiln-lO- dioxide by the Sandmeyer reaction I70 Preparation of 2-iodophenoxathiln-lO- dioxide from 2-amlnophenoxathlin- 10-dioxide 171 Reduction of the Sulfone Group by Lithium Aluminum Hydride 173 Preparation of phenoxathlin 173 Preparation of 2-chlorophenoxathiin 17^ Preparation of 2-bromophenoxathlin 175 • 'age Halogenatlon Reactions 176 Reaction of phenoxathlin with sulfuryl chloride in pentane 176 Preparation of 2-bromophenoxathlin and 2,8-dibromophenoxathiln by direct bromination (attempted) 179 Run I 180 Run II 181 Run III 181 Run IV 182 Run V 182 Run VI 183 Prepa,ration of 2-bromophenoxathiin-lO- dioxide by bromination of phenoxathiin- 10-dioxide (attempted) 18^ Preparation of 2-iodophenoxathlin-lO- dioxide by iodination of phenoxathiin- 10-dioxide 185 Oxidation Reactions 186 Preparation of phenoxathiin-lO-oxide by oxidation of phenoxathiin in ethanol with hydrogen peroxide (attempted) 186 Preparation of phenoxathiln-lO-oxlde by oxidation of phenoxathiin with dilute nitric acid 187 Sodium hypochlorite oxidation of 2,8- diacetylphenoxathiin to 2,S-nhenoxathiin- dicarboxylic acid 10-dioxlde 188 Preparation of l-phenoxathlincarboxylic acid 10-oxide 190 Preparation of 4-phenoxathilncarboxylic acid 10-oxide 191 Run I 191 Run II 192 Preparation of l,6-T)henoxathlindicarboxylic acid 10-dioxide 193 Preparation of 4,6-phenoxathlindlcarboxyllc acid 10-dioxide 19^ vl Page Preparation of 2-bromophenoxathlin-lO- dioxide by oxidation of crude 2-bromophenoxathiln 195 Preparation of 4-bromophenoxathiln-lO- dioxide by oxidation of crude ^-bromophenoxathiin 196 Cleavage Reactions 198 Hydrogenolyeis of 1,9-phenoxathllndl- carboxylic acid lO-dioxide 198 Run I 198 Run II 199 HydrogenolyeiB of 4,6-phenoxathlindi- carboxylic acid 201 Run I 201 Run II 202 HydrogenolyeiB of 1,6-phenoxathlindi- carboxylic acid 204 Cleavage of phenoxathiin by lithium, followed by hydrolyeie 206 Preparation of 2-thioldiphenyl ether by the reaction of sulfur with 2~lithiodiphenyl ether 207 Oxidation of 2-thioldiphenyl ether to bis-(2-phenoxyphenyl)disulfide 208 Preparation of 2-phenoxyphenylmercapto- acetic acid from 2-thioldipheiiyl ether and chloroacetic acid 209 Cleavage of phenoxathiin by lithium, followed by carbonation 210 DISCUSSION 213 Metalation Reactions 213 Acetylation of Phenoxathiin 22? Reactions of 2-Sub8tituted Phenoxathiin-lO- dioxides 229 Reduction of the Sulfone Group by Lithium Aluminum Hydride 230 vll Page Halogenation Reactions 23I Oxidation Reactions 236 Cleavage Heactione 238 Melting Points 2^3 Suggestions for Further Research 250 SUMMARY 256 ACKNOWLEDGMENT 259 1 INTRODUCTION Phenoxathiln (I) Is a compound which has been the sub­ ject of considerable Investigation by various workers who have not been concerned primarily with ItB chemical proper­ ties, Ae an antl-bacterlal agent phenoxathiln hae been tested for Its action upon Mycobacterium tuberculosis^'^. Escherichia coll^. Streptococcus hemolytloue (oyler strain)^, S. h. epldemlcuB^ and ^ vlrldans,^ The compound was shown to have slight anthelmintic activity against Haemonohus contortuB.^ The Insectlcldal properties of phenoxathiln have attracted the greatest attention. In one series of tests^ phenoxathiln gave high kills of American cockroach, cabbage aphid, diamond-back moth, European corn borer, Hawaiian beet webworm and termite. Other Insecte upon which phenoxathiln ^K. Tomlta and W. Watanabe, Jj;. Pharm. Soc. Japan. 71. 210i^ (1951)[ ^ As., 7618 (1952)X: ^M, Tomlta and V/. ^^atanabe, ibid.. 72. 478 (1952) [£:. As.. itZ. 7028 (1953)]. ^E, L, Everitt and M. X, Sullivan, ^ Wash. Acad. Sci.. 20, 457 (Wo). 4 H. McL. Gordon and M. Llpeon, Council Sci. Ind. Research. H, 173 (19^0). ^L. E. Smith, Ujj.^ Dept. Agr.. Bur. Entomol. end Plant Quarantine. E-580 {19 2 6 7 has "been tested are cattle lice , chicken lice , sheep 8 9 10-13 ticks , caterplllare and chl^ers. Phenoxathlln hae been shown to have larvacidal activity upon
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