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Syntheses and Reactions of Tetra- and Trisilyl- Substituted Organopolysilanes Clifford Leon Smith Iowa State University

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Syntheses and Reactions of Tetra- and Trisilyl- Substituted Organopolysilanes Clifford Leon Smith Iowa State University Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1966 Syntheses and reactions of tetra- and trisilyl- substituted organopolysilanes Clifford Leon Smith Iowa State University Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Organic Chemistry Commons Recommended Citation Smith, Clifford Leon, "Syntheses and reactions of tetra- and trisilyl-substituted organopolysilanes " (1966). Retrospective Theses and Dissertations. 3132. https://lib.dr.iastate.edu/rtd/3132 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]. This dissertation has been microfilmed exactly as received 67-5626 SMITH, Clifford Leon, 1938- SYNTHESES AND REACTIONS OF TETRA- AND TRISILYL-SUBSTITUTED ORGANOPOLYSTLANES. Iowa State University of Science and Technology, Ph.D,, 1966 Chemistry, organic University Microfilms, Inc., Ann Arbor, Michigan SYNTHESES AND REACTIONS OP TETRA- AND TRISILYL-SUBSTITUTED ORGANOPOLYSILANES by Clifford Leon A Dissertation Submitted to the Graduate Faculty in Partial Fulfillment of The Requirements for the Degree of DOCTOR OF PHILOSOPHY Major Subject: Organic Chemistry Approved» Signature was redacted for privacy. III Charge of Major Vorls. Signature was redacted for privacy. Signature was redacted for privacy. Dean oq Gi^duatk College Iowa State University Of Science and Technology Ames, Iowa 1966 il TABLE OP CONTENTS Page INTRODUCTION 1 HISTOBICAL 2 Tri- and Tetra-Group IVB-substituted DsrlTatlTos of Group IVB Compounds 2 Group IVB-substituted carbon compounds 2 Group IVB-substituted silicon compounds 9 Group IVB-substituted germanium, tin and lead compounds The Chemistry of Methylated Polysilane Compounds 19 Methods of preparation 19 Chemical properties 23 Physical properties 31 EXPERIMENTAL 36 A Direct Preparation of Some Tetrasllyl- substltuted Organopolysllane Compounds 38 Te trakl s( trlmetnyl sllyl) sllane 38 From silicon tetrachloride* chloro- trlmethylsllane and lithium in THF (general procedure) 38 Run 1 40 Run 2 41 Run 3 42 Run 4 42 Run 5 43 Run 6 43 Run 7 44 Run 8 44 Run 9 45 From silicon tetrachloride, chloro- trlmethyl sllane and magnesium in THF (att^npted) 45 Ill Prom silicon tetrachloride, chloro- trlmethylsllane and lithium in 1, 2, 3, 4-tetramethyltetrahydrofuran (attempted) 46 Tetrakl8(dimethylphenylsilyl)sllane 48 From chlorodlmethylphenylsllane; silicon tetrachloride and lithium in ÏHF 48 Prom dime thylphenyl silylll thlim and silicon tetrachloride 49 Tetrakls(triphenylsllyl)silane 50 Prom chlorotriphenylsilane, silicon tetrachloride and lithium (attempted) 50 A Direct Preparation of Some Trisllyl-sub­ stituted Organopolysllane Compounds 51 Tris(trlmethylsilyl)methylsilane 51 From methyltrichloro silane, chloro- trlmethyl silane and litbiium in THF (Bun 1) 51 Bun 2 51 Tris trlmethylsilyl 3# 59 6-tetra­ kl s( trlmethylsllyl)cyclohexen-1-yl - silane 52 From phenyl trl chloro silane, chloro- trlmethylsilane and lithium 52 Trls(dimethylphenylsllyl)methylsllane 53 From dimethylphenylsilyllithlum and methyltri chloro silane in THF 53 Tri s(trlmethylsllyl)silane 54 From trlchlorosilane, chlorotri- methylsilane and lithium in THF (attempted) 54 Trls(trlmethylsllyl)chloro silane (attempted) 55 From silicon tetrachloride, chlorotrl­ methylsilane and lithium 55 iv Reactions of Tetrakls(trlmethylsllyl)sllane 56 Tetrakls(trlmethylsllyl)silane with sulfuric acid 56 Tetrakls(trlmethylsllyl)sllane with aqueous plperldlne 56 xetrâkiâvtrimêthylëllyl)sllane with sodium methozlde in methanol 57 Tetrakls(trlmethylsllyl)sllane with bromine 57 Tetrakls(trlmethylsllyl)sllane with phosphorus pentaohlorlde 58 Tetrakls(trlmethylsllyl)sllane with methylllthlum 58 In THE*ether (4;l)(Run 1) 58 Run 2 59 In ether (attempted) 60 In ether at reflux (attempted) 60 With two equivalents of methyl­ llthlum in THF*ether (3*1) 60 Tetrakls(trlmethylsllyl)sllane with phenylllthlum 60 In THF*ether (4*1) 60 Tetrakls(trimethylsllyl)sllane with trlphenyl sllylll thlum 6l Reactions of Trls(trlmethylsllyl)sllylllthlum 62 General procedure for the preparation of trls( trlmethylsllyl)sllylll thlum 62 Trls(trimethylsllyl)sllylllthlum with trimethyl phosphate 63 Trls(trimethylsllyl)sllylllthlum wi th chlorodlmethylphenylsllane 64 Tris(trlmethylsllyl)sllylllthlum with chlo ro dlphenylmethylsllane 65 V Tris(trimethylsllyl)sllylllthlum wlth ohlorotrlphenylsllane 66 Tris(trimethylsllyl)sllylllthlum wlth ohlo ro dimethyl sllane 67 Tris(trlmethylsllyl)sllylllthlum wlth carbon dioxide 66 Trls(trlmethylsllyl)sllylllthlum with fluorene 69 General procedure for comparative metalatlons reactions of fluorene 70 Trls(trlmethylsllyl)sllylll thlum with THF 71 nie rate of reaction of ^ris(tri­ me thyl sllyl)sllylll thlum with THF 72 Trls(trlmethylsllyl)sllylllthlum with 1, 1, l-trlmethyl-2, 2, 2-trlphenyldlsllane 73 Tris(trlmethylsllyl)sllylllthlum wlth bromobenzene 74 Spectral Deteimlnation of Trls(trlmethyl- sllyl)sllylllthlum 74 Ultraviolet 74 N.m;r. 75 Oolor Test I of Trl8( trlmethyl sllyl )sllyl­ llthlum 75 General procedure 75 Preparation of Methyl Tris(trimethylsllyl)- sllanecarbozylate 77 From tris(trlmethylsllyl)sllane- carbcsyllc acld and dlazomethane 77 Preparation of B1s(trlmethylsllyl)methylsllane 78 From tris(trlmethylsllyl)methylsllane and methylllthlum 78 Reactions of Bls(trlmethylsllyl)methylsllyl- 11thlum 78 vi General procedure for the preparation of bi s(trimethylsilyl)methylsllyllithium 78 Bis(trimethylsilyl)methylsilyllithium with chlorodimethylphenylsilane 79 Bis(trimethylsilyl)methylsilylli thium with chlorodiphenylmethylsilane 80 Bis(trimethylsilyl)methylsilyllithium with chlorotriphenylsilane 81 Bi s(trimethylsilyl)methylsilyllithium with carbon dioxide 83 Run 1 (base extraction) 83 Run 2 (without base extraction) 84 Bis(trimethylsilyl)methylsilyllithium with fluorene S' General procedure for comparative metalatlon reactions of fluorene 85 Reactions of Bis(trimethylsilyl)methylsilane- carboxylic Aoid 86 Bi s(trimethylsllyl)methylsilanecarboxyli c acid with diazomethane 86 Pyrolysis of bis(trimethylsilyl)methyl- silanecarboxylic acid 87 Bi s(trimethylsilyl)methylsilanecarboxylic acid with 95^ ethanol 87 Reactions of Trls(trimethylsilyl)silane 88 Trls(trime thylsllyl)silane wi th n-butyllithium 88 Trls(trimethylsllyl)silane with methylllthium in ether 89 Tris(trimethylsilyl)silane with phenyllithium in ether 90 Miscellaneous Reactions 90 Trlphenylsilane and n-butylllthium in THF:ether " 90 vil Preparation of bis(trimethylsilyl)- diphenylsilane 91 From diphenyldiohlorosilane, ohloro- trimethylsilane and. lithium 91 Preparation of hexamethyl-2, 2, 3, 3- tetraphenyltetrasilane 92 Preparation of octamethyl-2, 2, 4, 4- tetraphenylpentasilane 93 DISCUSSION 95 A Direct Preparation of Some Tri- and Tetrasilyl-substituted Organopolysllanes 95 Tri sllyl-substituted compoimds 95 Tetrasilyl-substituted compounds IO3 Reactions of Te traki s( trlmethyl sllyl )silane 110 •Tri s( trlmethyl sllyl )silylll thium 114 Preparations and reactions of tris( trlmethyl sllyl )silylll thium 114 n-Bonding in tri s( trime thyl­ silyl )silylllthium 122 Color Test I of tri s(trimethyl­ silyl )silylllthium I34 Bi s( trlmethyl sllyl )methyl silylll thium I35 Preparation and reactions of bls- (trlmethylsllyl)methylsilylllthium I35 rr-Bonding in bls( trlmethyl sllyl)- methylsilylllthium I37 Physical Properties of Some Tri- and Tetra- silyl-substituted. Organopolysllanes I39 Spectral Properties of Some Tri- and-Tetra­ silyl- substituted Organopolysllanes 143 Infrared spectral properties 143 N.m.ri spectral properties 144 Till Ultraviolet spectral properties 148 SUMMABÏ 152 SUGGESTIONS POH FURTHER RESEARCH 155 LITERATURE CITED 158 ACKHOWLSDGSMENTS 166 1 INTRODUCTION Catenation of organoslllcon compounds was Initially studied by Pi S. Kipping and co-workers (1, 2, 3) about forty years ago; Despite the phenomenal growth of organoslllcon chemistry since that time, surprisingly few examples of sili­ con catenations were known before I960. (4, 5)* Since or­ ganically-substituted polysllane compounds have been found to possess a relatively high degree of stability, the paucity of organopolysllanes might well be attributed to the lack of equivalent methods of propagating silicon chains compared with carbon chains. Although the first branched»chain compound, lso=tetra= silane was formed in 19^3 (6) by a reaction between magnesium sillcide and hydrochloric acid, the compound was not Isolated until 1958 (?)• To date more than a hundred tri- and tetra- Group IVB-substituted organometalllc compounds have been pre­ pared and characterized. The objective of the woric presented here was to extend the boundaries of catenated organoslllcon chemistry to in­ clude the chemistry of some trl- and tetrasllyl-substituted compounds. HISTOBICAL Tri- and Tetra-Group IVB= substituted Derivatives of Group IVB Compounds Group IVB-substituted carbon compounds Although tetra-^butylmethane (I) is not known, in 19^7 Tyler, Sommer and Whitmore unsuccessfully attempted the pre­ paration of tri-t-butylchlorosilane (IX) and tetra-t-butyl= silane (III) by reactions between di-^butyldi chlo ro silane j^butyllithium (8), I II III %e synthesis of the first class of organosilicon compounds in which three or four silicon atoms
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