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Relative Reactivities of Some Organometallic Compounds Lester D Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1940 Relative reactivities of some organometallic compounds Lester D. Apperson Iowa State College Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Organic Chemistry Commons Recommended Citation Apperson, Lester D., "Relative reactivities of some organometallic compounds " (1940). Retrospective Theses and Dissertations. 13183. https://lib.dr.iastate.edu/rtd/13183 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 BELAflVI REAOflVITIES OP SOME OMANOHSTALlilO COMPOUNDS by Lester D. Apperson A thesis aateltted to the (Graduate Faculty for the Degree of DOCfOR OF PHILOSOPHX Major Subjeot Organic Chemietry Approved! Signature was redacted for privacy. In cha3%e of Major work Signature was redacted for privacy. or Department Signature was redacted for privacy. Dean of Qraduat® College^ Iowa State College 1940 UMI Number: DP12552 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 DP12552 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 QD-^-l I Ap48r AGKmvismmm fhe study of this problem was aided materially by the valuable suggeetlons given by Dr. Heoary Oilman. ti ( - 3 - TABLE OP CONTENTS Page inmomGfion. s A» ORQ-AMOALUMINUM HAI.IDE8 10 HISfORlCAli, 10 Simple Organoaluainuia Gospounds. 21 SXPERIMKl^AL, 30 Preparation of EthylalximinuiB Chlorides... 30 Preparation of Diethylaluiainum Chloride. 31 Preparation of Sthylalumimim Bichloride. ... 32 Preparation of Ethylaluminum Iodides 33 Preparation of Butylalumlnum Iodides........... 34 Preparation of Mixed ButylalualnuES Chloride mhemtee, 35 Preparation of Phenylalumlnua Iodides. 36 Preparation of jg-folylaluaiimm 0iohloride...... 37 Miscellaneous Attempted Preparations of Organoaluffiiimm Halidee — .... 38 Reaotions of Mixed Ox^anoaluminiim Coapounds,... 38 Color feet with Michler'e Ketone 39 Benzonltrlle and Phenylaliminwai Iodides... 39 Benzonltrlle and Ethylaluralnum Iodides.... 41 Oarbonation of Hthylaluminm Iodides...... 41 Carbonation of PheE^rialuiaintim Iodides..... 41 Ketones and Organoaluminam Halides... 41 Benzophenone*Aluminum Chloride Complex and Oi^anoaluminua Iodides — ..... 42 - 4 ~ Aoetophenoiie-AluffiliniBi Clilorlde Oonplex and Organoaliimijauia Iodides 43 Aoetoph©none-Aluala\im Chlorld© Complex and Sthylaluffilnua Chlorides.... ... 44 Proplophenone-Aluffilnus Chloride Complex and Sthylalumlnum Iodides ..... 44 Aoetone-Aluralnua Chloride Complex and Organoaluminiiia Iodides. 45 Benzoyl Chloride-Aluialnua Chloride CoHiplex and Sthylaluiilmim Iodides 45 Benssoyl Chloride-Aluainuffi Chloride Complex and Fheiiylaluminuia Iodides. 46 Benzoyl Chloride-Aluainuffi Chloride Complex and ^folylaluminum Diohloride............ 47 Aoetyl Chloride-Aluminum Clilorlde Coaplex and _^folylaluHlnuffi Di ohloride............ 47 Benzoyl Chloride and Ethylaluaiinua Iodides..... 48 Benzoyl Ohloride and Phenylaluainum Iodides.... 49 Benzoyl Chloride and Trlphenylaluiainua......... 50 Benzoyl Chloride and Diethylaluminum Chloride 51 Benzoyl Chloride and Sthylaluffiinuaa Dlohloride- Sodium Chloride iJouble Salt. 51 Benzoyl Chloride and _£-Tolylalumlnuia Olohlorlde 52 Benzoyl Iodide and Phenylaluminu© Iodides...... 53 Benzoyl Iodide and Ethylalumlnttai Iodides 54 Acetyl Chloride and p-Tolylaluainuia Diohloride 54 Aeetlo Anhydride and EthylaXuslnuia Chlorldee... 55 Benzolo Anhydride and Ethylaluialnuffi Iodides.... 55 - 5 - Benzenesulfonyl Chloride and Ethylalumiaim lodidea. 56 Cstr^n f etraohlorid« and Benzene in the Presence of Ethylaluaintua (^orides*. 57 DISCUSSION OF RESULTS S9 i^eparation of Organoaluiainum Halldes.. 59 Eelatlv® ReactiTitles of Simple and Mix«d Os^anosetallic Compounds 63 Relative ReaotiYities of Simple and Mixed Oi^aiKisluffilnuja Compounds 65 Relative Reaotivities of RgALX and RAlX® Coiapounds, TO Relative Reactivities of Alkyl- and Aiylaluminum Halidee 70 Effect of &)lvent on the Reaotivity of Oi^anoaluiainua Halidea. 71 Relative Reaotivities of Benzoyl CSiloride and Benzoyl Iodide toward Orgajaoalumlnum Halides. 72 Ox^anoaluminuB Compounds and the Friedel- Crafta Reaction. 73 Ketone-Aluminuffi Chloride Oomplexes and Organoaluaiatjia Halide®............... 77 Acid Chlorida-Aluffiinuffl Chloride Complexes and Organoaluffiinum Halldes. 78 Aoid Chlorides and Organoaluainuo Halidee. 90 Aoid Anhydrides and Organoaltiminu^ Halidea 81 SU»!AK5f 85 B. DITALIKT OR(JANOLEAD RADICAl^S. 86 HI^ORICAL. 86 Divalent Organogenaaniiua Radicals. 86 ~ 6 - Divalent Organotin Radicals. 87 Divalent Organolead Radioals 93 SXPERIHEim 94 Phenylaagnesium Bromide and Lead Ghlorid© 94 ^folylffiagnesium Bromide and Lead Chloride 96 Cyolohexylaagnesium Chloride and Lead Ghloride, 98 Reactions in Liquid tomonia Between RgPhXn Compounda and fwo Equivalents of Metal.... 99 Dicyolohexyllead Dibromide and Sodium 99 Diphenyllead Difluoride and Lithium. 100 Diphenyllead Diohloride and Lithium. 101 Diphenyllead Dibromide and Litliiua......... 102 Diphenyllead Di-iodide and Lithium......... 103 Diphenyllead Dibromide and Lithium in Ethers Liquid AiBffionia 102 Reactions in Liquid ilismonia Between R,FbXa Compounds and Pour Skjuivalente of Metal... 105 Diphenyllead Dibromide and Lithium. 105 Diphenyllead Dibromide and Sodium 108 Diphenyllead Dibromide and Potassium. 109 Diphenyllead Dibromide and Caloius,........ 109 Diphenyllead Dibromide and Strontium....... 110 Diphenyllead Dibromide and Barium 110 Diphenyllead Di-lodide and Lithium. Ill Diphenyllead Difluoride and Lithium........ 112 Diphenyllead Diohloride and Lithium........ 112 friphenyllead and Three Ecfuivalents of Sodium. 115 7 - Mlithluffi Diphenyllead and Aiamonlum Bromide..,. 115 Attempted Isolation of DilitMua Diphenyllead.. 117 aillthium Diphenyllead and Diphenyllead Dibroffiide. 117 Reduction of Diphenyllead Dihalides by Hydrogen 118 Diphenyllead Diohloride and Aluminum 120 Diphenyllead Diohloride and l^drazine K^drate.. 120 Lead Meroaptide and Phenyllithiiaa. 130 DISGUSSIOM OF RESULTS. 1S3 SIMARY 133 8 ^ IMTEODUCTIOS ©aapoiaads are pjrobably tfee mmt Importaat gi*6iip Gf oo^KKttsae used la orgaiiio syathesi®, fh®^ iaalmfi© all oomps^iiAs «hioJi eontaia a direot ualos ©f ©arbon with a 25it® two main ©lasses of oi^anometallle ©oiapcsiuMs af© somonly kaowft at ''simple* and *raixed". A simple org&norattallie ®oi^>oim4 ia om whieli has only E gyoupg attaehea to the mstal {Ra%) wMle a mixed oi^anjoraetallie oompound has both R aM X gs»oupe attached to the metal (HMgJC), fhe I group is uau- ally % halogen altlioiigh it aay b® aa aeid radioal# hydrogen, hy4mxrl» aaitto or one of a variety of other groups depending upoa the reaotlTit^r of the seleotefl organoiEietalli© eoi^md. fhe a gK3«p is generally an alkyl or aiT'l radical ana. it m&j eontain a la2se variety of substituents, but the aubatituentg are obvioualy limited to those ^li^ will mot reaot with tJie shosea organometallis oompound. fflbis simple ox^aaosjetallio ooiapounda may be further classified into aysaatrioal and wnsymraetrioal /TCaHs)gPbG« Hi? gitjups, to additional olasslfioation is bastd upon the ^alehoe ©f th# metal in th© organoiaetallio ooBpound, The teiia *or^an©~ sttallio radical* is given to thosa organometallic oompounds which oontain the metal in a lower valenoe state than is nor* m&l for th® metal, ^eh ooffipouads are characterized by their t@nd«ney to rsvert to eospounds oontaini«g the metal in its HGsmal valeno® state. A kaoirledge ©f the nO-ative reactiTitles ©f orgaaoaetalll® ©offipouMs is not only of theoretioal interest, Mt it also aide in the seleetion of th© proper organotaetalli© ©ompownd for use in a particular synthesis, asyntheses often involve the use of seleetive reaotlons, fhe wide range of reaotivities eahihited W o^anoffietallio ©ompmindB should make ^lem exoellent reagents for effeetii^ preferentli^ reaotiona with polyfunotional ®oia» pound®. First, of eourse, experimental data on th© relative reaotivities of the individual organometallle eoapoands sust be oomplled before the proper si^eetions for preferential reaetions can be made. !ltoe present w>rk wit3i organoalusinuiB halides iias under- taken with the view of eoMparing their reastivity wife sii^le ©rganoaluffiiima oompounds and with organojaetallle Qompmnds ia general, fhe possibility of the iaterffiediate formation of organoaluffiimuB halides in the Friedel^Orafts reaction has s^so been considered. fhe studies on divalent ox^anolead radieals were under-* talLea with the aual purpose
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