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Preparation and Basic Cleavage of Some Arylsilanes Lewis Samuel Miller Iowa State College

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Preparation and Basic Cleavage of Some Arylsilanes Lewis Samuel Miller Iowa State College Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1950 Preparation and basic cleavage of some arylsilanes Lewis Samuel Miller Iowa State College Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Organic Chemistry Commons Recommended Citation Miller, Lewis Samuel, "Preparation and basic cleavage of some arylsilanes " (1950). Retrospective Theses and Dissertations. 13719. https://lib.dr.iastate.edu/rtd/13719 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 PREPARATIOII AIJD BASIC CLEAVAGE OP SOLE ARILSILAKES by Iiewls Samuel Killer A Dissertation Submitted to the Graduate Faculty in Partial Fulfillment of The Requirements for the Degree of DOCTOR OP PinLOSOPHT Major Subject: Organic Chemistry Approved Signature was redacted for privacy. In Charge of Major Work Signature was redacted for privacy. Head of Major Departiien' Signature was redacted for privacy. Dean of Graduate College Iowa State College 1950 UMI Number: DP12853 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 DP12853 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 ACKlIOWLEDGEBffiHT The author wishes to express his appreciation to Dr. Henry Gilinan for the advice, criticism, and encouragement given throughout the course of this investigation. T95/9 ill TABLE OP CONTENTS Page ACKNOWLEDGMENT il IliTRODTJGTION 1 HISTORICAL . ; i}. •' I cleavages of Organosilicon Compounds / by* Basic ;or Nucloophilic Reagents . • • . • I4. Cleavages of OrganomDtallic Corpoxinds by Basic or Nucleophilic Reagents • • . 26 Cleavages by V/atcr, Alcohols, or Bases • • • 26 Metal-metal Interconversion Reactions • • . 3!^ EXPERMHTAL i}.8 Organosilicon Confounds 1^8 Tris-(£"*chlorophenyl)-ethoxysilane ij.8 Iexakis-(£-chlorophenyl)-disiloxane .... 49 Tris-(£-chlorophenyl)-silanol lj.9 jrocedure for the Microdetermination of Silicon ........... 50 ?etralcis-{£»chlorophenyl)-silane ...... $0 Phenyltriethoxysilane •«... $1 henyl-tris«p«(£-chlorophenyl)-silane .... 51' 'riphenyl-bis-{£«chlorophenyl)-silane . 52 ^^rlphenyl-(£-chlorophenyl)-silane ..... 52 - ethyl-trls-{^-chlorophenyl)-silane . • . 53 (Trichlorone thyl)-triS "'{£"-chlorophenyl)- silane 5^ 3iraethyl-bls-(ja-chlorophenyl)-silane .... 55 rkj. Prom Diraethyldichlorosilane 55 Prom Din^ toyIdiethoxysilane . 55 Direct Chlorination of I^iEisthyl-bis- {^-chlorophenyl)-silane •»••••.. 5^ Chlorination of Dime thyl-bis-(£»»chloro» phenyl)-silane with Sulfuryl Chloride . 57 Page Organosllicon Compo'unds (continued): Iitethyl-{ trlchloronieth7l)-dic}2lorosllane • • • Methyltriphenylsllane • *,/• • 59 C,3?X'ichlororaetliyl)-triphenylsilane . 59^' /^'£-Dodecyl-tris-(je-chlorophenyl)-silane • . 62^' "T,3-DiTn© thyl-1,1,3 , 3- te traki s- (^-chlorophenyl)-dlsiloxanc 6' Trlphenyl-{£-a2ninoplaenyl)-silane (Attempted). 61 /-n-Propyltriphenylsilane •..« 6^ ij-Arayltripiienylsilane Go ^:^*Hexyltriphenylsilane 6Q Triphenylbenzylsllane 68 ^riphenylbenzoliydrylsilane 69 '^Triaethyl-9-i'1^03^n.yisilane •«•«••... 70 - i Triphenyl-9**i'l^o^®iiylsil8J^® 70 ^-Phenyls tiiyllithitim ............ 71, Triphenyl-( J-phenylethyl)-silane 72^ / Tpiphenyl-tphenylethynyl)-silane 72 ^riphenyl-l-indenylsilane 73 '^^l-Bis-(triphenylsilyl)-indene ....... 74- ^Viphenyl-(s-trlfluoroinothylphenyl)-silane. m ^ ^Tetra-«•naphthylsilane (Atten^jted) ..... Jo Reaction of (Trichloroiaethyl)-trlphenyl- silane with Three Equivalents of Ji-Butyllithium JQ ) Reaction of (TPiiC!hloronethyl)-triphenyl- silane with Tliree Equivalents of PhenyllithiuEi 79- / Triiae t^l-(triphenyliae thyl)- silane / L KJ' Pron TriphenylroethylsodiTAia ... 79 r^j. Pron Triphenylraethylllthium ... 80 ^c"7« Prom TriphenylmethyImagneslum Chloride 82 Cleavage of Trine thyl-(tripheny line thyl)- silane v/ith Hydrochloric Acid (Attexnptcd) 83 Cleavage of Trimethyl-{triphenylmethyl)- silane v^ith Aqueous Potassium Hydroxide in Acetone .....•• 83; Triphenyl-( triphenylme thyl)-si lane (Atteirpted) 83^ Tri-H-tolylcarbinol 87 Tri-£-tolylinetliane 88 Tri-ja-tolylmethyllithiura £"(l>-0HaCaH4 )3CLi_J7* 88 Trlphenyl-( tri-E-tolylmethyl)-silane (Attempted) 88 Bls-(£-broraophenyl)-phenylcarbinol 89 Big?>(g-broinophenyl)-phenyline thane ...... 90 s"£ £- (triphenyl s1 ly 1) -pheny 1_7"* phenylcarbinol ............. 9I V Page Organo^l^on Coiapounda (continued); , S~(triphenyls lljl)-phenylj/" phenylEKjthane 92 Basic Cleavage Reactions 92- Reagent (A). Cleavage of Triiaethyl- phenylailane (Attenpted) •«.•••. 93; Reagent (B)« Cleavage of Trlphenyl- benzylsllane •••.. 93 Reagent (C). 100 Reagent (D)• Cleavage of Triphenyl- benzylsilane 101 Silanol Titrations with the Fischer Reagent ... 102 Preparation of the Fischer Reagent . 102 Silanol Titrations «.. ..... 102 '^^^^i-j)'"3cenylroethoxysilane •.••....•• loi|. Titrations of Triphenyllead Hydroxide, Triphenyltin hydroxide, Phenylboric Oxide and Phenylboric Acid lolj. /Triphenyl-^-butoxysilane .......... 105 Discussion . 107 Organosilicon Coinpounds 107 Basic Cleavage Reactions ••.... 112 Silanol Titrations v/ith the Fischer Reagent ... 12^ SUIfffARY 129 1 IKTRODT'CTTON Many Investigations have been reported whose ultimate purposes have been to establish a general series by which the relatix'e ease of cleavage of organic radicals from netals could be predicted^, Silicon, although not generally considered to be a netal, has been fo^md to behave in a manner qualitatively analogous to the inetals in these cleavage I'-sactions. The major part of this work has ei^iployed acidic or electrophilic reagents such as hydrogen chloride, the halogens, or metallic halides. This type of cleavage reaction of organometallic compounds has been I'eviewed recexitly by P. J. Marshall 2. The use of metals as cleavage agents has been reviewed by Bindschadler-^ and Ilaubein^. The basic or nucleophilic cleavage reagents have received relatively less attention by investigators, although enotogh work has been done to indicate^khat the order of ease of cleav­ age of the radicals from metals is often considerably different ^Por general references, see (a) Gilman, "organic Chemistry, An Advanced Treatise" , Jolm V/iley and Sons, Ilew York, 19l4-3» pp. 1|.89-579» (1^) Krause and von arosse. Die Chenie der metallorganischen Verbindtmgen , Bomtraeger, Berlin, 1937• Marshall, Doctoral Dissertation, Iowa State College (19lf8). See also oilman and Marshall, jj;, Chern* Soc,. 71. 20o6 (19l{.9). 3 Bindschadler, Doctoral Dissertation, Iowa State College (19l|-l). aubein. Doctoral Dissertation, Iowa State College (I9I4.2). 2 from that obtained with acidic reagents. The literature records few concerted studies of this type with the exception of soi3Te fairly extensive v7orl: which has been done on cleavages of one organometallic reagent by another, the iiiotal-iiietal interconversions. "Ehe early work of this latter type, covering derivatives of a large range of iietals, is STOirKmri-ed briefly by Jones^. Fairly extensive investigations have also been carried out in recent years on the basic cleavage of various halogen- or oxygen-substituted allcylsilanes. Kie purpose of the present investigation v/as to extend tiiese basic cleavage studies to the field of aryl- and mixed allcylaryl-silanes. In addition, an atten^jt was mde to show a correlation between the acid strength of a hydrocarbon (as determined in studies by Conant and VYheland and others^),A and the ease witii which the corresponding carbanion could be cleaved from silicon by a nucleophilic reagent, the radicals corresponding to the carbanions of the stronger acids splitting off more readily^ Many of the arylsilanes vi&ich were made were previously unlaiovm, and extensive applications of organolithium reagents wero purposely used in their preparation in order to extend our knowledge of these versatile organometallic compounds. ^Jones, Doctoral Dissertation, Iowa State Colle ge {19i|l). ^Conant and VVheland, jJ. Chem. Soc.. 1212 (1932); BtoEwen, ibid,. ^^8. 1121}. (1936). 3 Another group of organosllanes was prepared v/hlch contains groups present in active insecticides and these cotapoimds were submitted to Dr. C. H. Ricliardson^ for evaluation in order to cojiipare their insecticidal activity with tliose of related carbon analogues. 'Department7 of Entomology, Iowa State College. i}- mSTORIGAL The following survey sxCTiarizes the work doscribod in the literature in which a carbon-to-sillcon or carbon-to- Kiotal bond has been cleaved by a basic or nucleophilic re- ageiit. A nucleophilic roagont
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