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The Introduction of Functional Groups Into Some Organosilanes Russell N Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1946 The introduction of functional groups into some organosilanes Russell N. Clark Iowa State College Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Organic Chemistry Commons Recommended Citation Clark, Russell N., "The introduction of functional groups into some organosilanes " (1946). Retrospective Theses and Dissertations. 13393. https://lib.dr.iastate.edu/rtd/13393 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 •mi IMTRODUGTION OF PUNCTIOHAL GROUPS INfO SOME 0RGAN08II.ANgS Rttseell K. cn.ark A fhesla Sul^ltted to the Graduate Faculty for the Degree of DOCTOR OF PHILOSOPHT Major Subject: Organic Ohemlsti^ Approved; Signature was redacted for privacy. Signature was redacted for privacy. Head of Major Deparfeent Signature was redacted for privacy. Hean of Graduate College Iowa State College 1946 UMI Number: DP12644 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 DP12644 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 11 c^4-; ACKNOWLEDGMENT author Is eincerely grateful to Dr. Henry Q-llman, whose valuable suggestlone and encouragement have been of great assistance during the course of these studies. r^o ^ ill TABLE OP CONTENTS INTRODUCTION NOMKNGLATURE HISTORIGAL • • • A. A Brief Review of Organoslllcon Cheraistiy from 1863 to 1927 B. Organosilioon Chemistry from 1937 to 1945 Introduction Alkyl Derivatives of the Type H^Si , , Alltyl Derivatives of the Type E'R^Sl . Aryl Derivatives of the Type R^^^i • • Aryl Derivatives of the Type R*RgSi , , Alkyl Derivatives of the Tsrpe RSlXg . , Aryl Derivatives of the Type RQiX^ . Alkyl Derivatives of the Type RgSlXg . Ai^l Derivatives of the Type RgSiXg , . Allsiyl Derivatives of the Type RR'SiXg . Mixed Aryl-Alkyl Derivatives of the Type RH^SiXg Alkyl Derivatives of the Type R^SiX . , Aiyl Derivatives of the Type R^SiX . • Alkyl Derivatives of the Type RgR'SiX . Alkyl Derivative.^ of the Type {RO)^Si . Aryl Derivatives of the Type (RO)^Si . iv Pag© Alkyl Derivatives of the Type (RO)gSiOR', 3I Mixed Aryl-Alkyl Derivatives of the Type (RO)_SiOR' 45 O Alkyl Derivatives of the Type (ac igSiCOR*)^ Mixed Ai'vl-Mkyl Derivatives of the Type (RO^gSKOROg .. » Alkyl Derivatives of the Type R3i(OR')j5 Aryl Derivatives of the Type RSi(OR)„ • O Alkyl Derivatives of the Type RgSiCOR') Aryl Derivatives of the Type R^SiCOROo /Z Alkyl Derivatives of the Type RR*Si(OR")g Mixed Aiyl-Alkyl Derivatives of the Tjrp® RR'Si(ORO Alkyl Derivatives of the Type R^SiOR' Aryl Derivatives of the Type RgSiOR' Alkyl Derivatives of the Type R§iOR' Alkyl Derivatives of the Type ROSiXg Aryl Derivatives of the Type ROSiXg . Alkyl Derivatives of the Type (R0)2SiXg Aryl Derivatives of the Type (R0)pSiX2 Alkyl Derivatives of the Type {R0){R'0)CiX2 . Alkyl Derivatives of the T?/pe Aryl Derivatives of the Type (R0)331X . .Hkyl Derivatives of the T;^/pe (R0)(R'0), Six ' V Alkyl Derivatives of the Type Paf-e Q (R-a-0)j,SiY^^^j^ 70' Alltyl Derivatives of the Type R^SlNRg . 72 Alkyl Derivatives of the Type {RS)^_S1 . 73 ' Alkyl Derivatives of the Type (RS)pSl(SR*)^ •••• 75 t-./ Alkyl Derivatives of the Tyne (HS^^SlCOR') 75 Alkyl Derivatives of the Type (RS)23iX. 75 Alkyl Derivatives of the Type (H3)gSlXp . 76 Alkyl Derivatives of the Type RSGIX^ . 76 Alkyl Derivatives of the Tyoe Iw31-0-31R^ 76 o o Aryl" Derivatives of the Ty:oe R„3103111^. « 78 o o Alkyl Derivatives of the Type /rR0)gJ^7oC. 79 Alkyl Derivatives of the Ty_)e /R0(R'0)gSj720 80 Alkyl Derivatives of the Type /Rgll'01337^0 31 Alkyl Derivatives of t}iG Type Hi[^her Liner r 611ozane Derivatives ... 81 Alkyl Derivatives of the Type • 82 Alkyl Derivatives of the Type R^SI-SIR^ . 83 v Aryl Derivatives of ttie Type R^SI-SIR^ . 84 Silicon Polymers 35 EXPERI1.1ENTAL 93 A. Silicon Compounds . .••••• 93 vl Pa^je ^ ITetraethylsllane 93 Tetra-n-butylsllane 94 TetralBopropylsllBue (Attempted) .... 95 Tetra-t-butylsllane (Attempted). ...» 97 ^Tetraphenylsilcoie ........... 98 /^rlphsnyl-^-tolylsllaiie 99 /Trl-2-"fcolylphenylsllane 100 J^-PlQolyltrlphenylsllane (Attempted). , 100 Dlphenyldi-j^-tolylsilane lOE /ferlphenylmethylsilane 1S3 /yrlmethylphenylsllane 104 / •^•riphenylolleiiol .....•«•*••• 104 -^rlphenylethoxysilane 105 'irlmethyl-j^broBJophenylsllane ..... 106 Trlmethyl-j3-llthiophenylBilane ..... 108 /Benzyltriethoxyailane ......... 103 '^frJjBethylbenzylsllane 110 Attempted biHsmination of trlnetl-iyl- benzylailane . Ill Attempted nitration of triraethylbenzyl- silsjie 112 Phenyl trie thoxyallane 113 Attempted nitration of phenyltrlethoxy- sllane ,,... ........ 114 • p-AolnophenyltriethoxyQilane ...... 114 J^riethylohlorosilane ... ...... 116 vll Page Refonuatslcy reaction with trlphenyl- chlorosllane ...» 116 Refortnatsky reaction with trlethyl- cJilorosllane ..••••••«.•• 117 Etliyl trlethylsllylacetete (Atterrpted). 117 Ethyl trlphenylsilylacetate (Attempted) , 118 Reaction 'oet^een trleth^^-lchlorosllane and ethjl sodloacetoacetate ...» 118 Reaction of trlphenylcjilorosllaJie and ethyl sodloacetoacetate 122 Reaction hetr-'C-on triphenylcliloronllrne sud diethyl socllonalonr.te ..... 122 Reaction of trlethylclrilorosllajie viith diethyl sodiomelonate 123 B. ^-Lactame of yi-ARlllno- i^-phenyl- proplonlc Aclae ............. 123 i^-Lactara of /6-an 11 lno-/4-phenyl- propionic acid • . • 123 Basic hydrolysis of the /^lactain of ^aiillino- y5-phenylproplonic acid. 124 Acid hydrolysis of the ^lactan of ^enlllno- ^-p}ienylpropionic acid . 124 Ethyl ^anlllno- /J-phenylpropionate . 125 Ethyl ^-anillno-/^ ~phenylpropionate ... 125 Reactlon'-^of ethyl ^anllino-/5-phejiyl- propioiiate with methylmagneslum iodide 126 Reaction of ethyl ^anlllno-/^-phenyl- propionate with n-butylllthluin ... 127 Reaction of ethyl y^anillno-/^-phenyl- propionate vjith lithium diethyla^ilde 127 Reaction of ethyl i^anllino-/^-phenyl- propionate wixh dlethylzinc . ... 127 vlll i» y» Reaction of eti^ayl fl-anlllno- fVphenyl- proplonate with phenylllthlum . • * • 128 Reaction of ethyl (^anlllno-A-phenyl- propionate with Ejethyllithium .... 128 Reaction of ethyl [Vanlllno-^-phenyl- propionate with phenylethynylmagnesli® iodide 129 Reaction of ethyl /^anlllno- /i-phenyl- proplonate with phenylethynylllthiura. 129 Acetosesityl^e 130 Reaction of ethyl /3-anilino- /3-phenyl- proplonate with aoeto/m eeltyl- magnesliaa brcaaide , . 130 Variation of solvent in the preparation of the /J-lactaiB of >^anilino<-A-phenyl- propionic acid 130 Variation of the zinc employed in the pre­ paration of the y^lactao of ^anllino- ^-phenylpropionic acid ....... 131 o-Chlorobenzal-^-chloroaniline ...... 131 I^Lactara of As-chloroanilino- /5-o - chlorophenylpiHspionic acid ..... 132 ^-Anlflal-£-anisidine 132 ^Lactam of ^£-anieidino-/^-jg-anisyl- propionic acid . 132 _2-Anisal-^chloroaniline 133 A-Lactam of /5-^-chloroanillno->4-j2- anlsylpjfopionic acid 133 ji-Anisal-ra-chloroaniline 134 A-Lactam of A-m-chloroanillno-^ ' anlsylpifoplonic acid ........ 134 £-Ani8al-o-chloroaniline 134 Ix Page Attempted preparation of the ^lactam of A-o-chloroanlllno- ^ -£-anisyl- pi^pionio acid ........... 135 o-Chlorobenzal-o-ohloroanillne ..... 135 Attempted preparation of the ^^lactaa of /i-o- chloroan il Ino- /^o- cnloro- phenylpropionic acid T ...... 135 Benz.al-^-chLoroaniline ......... 136 ^-Lactam of chloroanilino- ^-phenyl- propionlo acid 135 Benfcal-p-ani0iaine ........... 136 ^-Laetaai of /i-£-anisidlno~ id-phenyl- propionic acid 137 D-ChloiKJbenzalaniline 137 A-Lactam of /5-anilino- A-£-chloro- phenylpropionic acid 137 H,N*-Benzal-bis-JL-pyridylaiaine ..... 138 Benzal- Ji -pyridylamine 138 Attempted preparation of the /^-laetam of -A.-pyridylRinino-/S-phenylpropionic acid ' 138 Attenrpted preparation of benzal-o-chloro- aniline .........T .... 139 Benzal-o-ohloroaniline 139 Attemoted prepsj^ation of. the/^lactam of A-o-cnloroanilino- A-phenylpropionio acid . ' ~. 140 C. Phenylpyridlne Derivatives 140 2-Phenylpyridlne ...... ...... 140 E-Nitrophenylpyridinee ......... 140 X Page 2-(4•-AsInophenyl)pyridine 141 2-(4•-Benzalarolni phenyl)pyridine . • • 142 2-(4*-SalloylalejBlnophenyl)pyridlne « • 142 '-Z4'~(2", 5"-Dimethylpyrryl-l" )phenyl7- pyridlne .......... ... 142 2-(4'-FormylanInophenyl)pyrldine • • • • 143 2-(4'-Acetartiinophenyl)pyrldlne . « • • 143 2-(3' -IIitro-4 *-acet02ninophenyl} pyridine. 144 2-(5'-nitro-4'-aifllnophenyl)pyridine « • 145 2-(u *-Hitro-4 Inophenyl )i)yridjln e 145 jj-Anlsylllthlum ..•••••••••*
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