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The Direct Electrochemical Synthesis of Selected Group-Iib Organometallic Compounds

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The Direct Electrochemical Synthesis of Selected Group-Iib Organometallic Compounds University of Windsor Scholarship at UWindsor Electronic Theses and Dissertations Theses, Dissertations, and Major Papers 1-1-1979 THE DIRECT ELECTROCHEMICAL SYNTHESIS OF SELECTED GROUP-IIB ORGANOMETALLIC COMPOUNDS. AKHTAR OSMAN University of Windsor Follow this and additional works at: https://scholar.uwindsor.ca/etd Recommended Citation OSMAN, AKHTAR, "THE DIRECT ELECTROCHEMICAL SYNTHESIS OF SELECTED GROUP-IIB ORGANOMETALLIC COMPOUNDS." (1979). Electronic Theses and Dissertations. 7187. https://scholar.uwindsor.ca/etd/7187 This online database contains the full-text of PhD dissertations and Masters’ theses of University of Windsor students from 1954 forward. These documents are made available for personal study and research purposes only, in accordance with the Canadian Copyright Act and the Creative Commons license—CC BY-NC-ND (Attribution, Non-Commercial, No Derivative Works). Under this license, works must always be attributed to the copyright holder (original author), cannot be used for any commercial purposes, and may not be altered. Any other use would require the permission of the copyright holder. Students may inquire about withdrawing their dissertation and/or thesis from this database. For additional inquiries, please contact the repository administrator via email ([email protected]) or by telephone at 519-253-3000ext. 3208. 492-33 National Library Bibliothfeque nationale CANADIAN THESES THESES CANADtENNES f l * .of Canada ~ du Canada ON MICROFICHE SUB UJCBOFICHE NAME OF AUTHOR/NOM O f L’AUTEUR. A khtar Osman TITLE OF THEStS/7777?£ O f LA THESE- The direct electrochemical synthesis of selected grouo IIB organonetallic compounds. UNIVERSITY/LW/ VERS/ TE. U niversity of ~Windsor. Windsor ..Ontario DEGREE FOR WHICH THESIS WAS PRESENTED/. GRADE POUR LEQUEL CETTE THESE FUT PRESENTEE _ Ph.D. YEAR THIS DEGREE CONFERRED /A NNiE D'OBTENTlON DE C£ GRADE Mav 19 SO NAME OF SUPEKVISOR//VOM DU D1RECTEUR DE THESE _ U r. D. G. Tuck Permission is hereby granted to the NATIONAL LIBRARY OF Cauterisation est. par la presents. accordde 3 la BIBLIOThE- CANADA to microfilm this thesis and to lend or sell copies QUE NATlONALE DU CANADA de microfilmer cette thdse el of the film. de prSter ou de vendre des exemptaires du film. The author reserves other publication rights, and neither the L‘auteur se reserve les autres droits de publication: ni la th esis nor extensive extracts from i.t may be printed or other­ thiseni de longs extraits de celle-ci ne doivent etre imprimis wise reproduced without the author’s written permission. ou autrement reproduits sans.Tautorisation.dcrite /*deauteur. I na.T?n/nATE ^ . i SIGNED /SIGNS. PERMANENT ADDRESS/RESIDENCE FtXt. N I.-9I CS-74* Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. 9 1 + National Library of Canada BiWioth^que nationals du Canada. Collections Development Branch Direction du developpement des collections Canadian Theses on Service des th&ses cana ennes Microfiche Service .. sur microfiche L NOTICE AVIS The quality of this^microfiche is heavily dependent La- qualite de cette gr^ndement de upon the quality of the original thesis'submitted for la qualite de la these fofilmage. Nous microfilming. Every effort has been made to ensure avons tout fait pour une qualite superieure the highest quality of reproduction possible. de reproduction. If pages are missing, contact the university which 5'il manque / des \)ages, veuillez communiquer granted the degree. aved l'universite qui a coqfere le grade. Some, pages may have indistinct pr-lnt especially La qualite tfimpression de certaines pages peut if the original pages were typed with a poor typewriter laisser a desirer,'surtout si les pages originales ont ete ribbon or if the university sent us. a poor photocopy. dactyiographiees a I'aide d’un ruban use ou si I'univer- site nous a fait parvenir une photocopie de mauvaise qualite. Previously copyrighted materials (journal articles, Les documents qui font deja I'objet d'un droit published tests, etc.) are not filmed. d'auteur (articles de revue, examens pubties, etc.) .ne sont pas microfilmes. Reproduction iry full or in part of this film is gov­ La reproduction, meme partielle, de ce microfilm erned by the Canadian Copyright Act, R.S.C. 1970, est soumise a la Loi canadienne sur le droit d'auteur, c. C-30. Please read the authorization forms which SRC 1970, c. C-30. Veuillez prendre connaissance des accompany this thesis. formules d'autorisation qui accompagnent cette these. THIS DISSERTATION -LA THESE A ETE HAS BEEN MICROFILMED MICRyFLLMEE TELLE QUE EXACTLY AS RECEIVED NOUS/ L' A "ONS RECUE Ottawa, Canada K 1 A 0 N 4 NL-339 {Rev. S/80) Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. THE DIRECT ELECTROCHEMICAL SYNTHESIS OF SELEe?ED GROUP' IIB v ORGANObETALLIC COMPOUNDS)^£TALL] . by . ■ C Akhtar Osman B.Sc., University of Karachi, 1970 M.Sc., University of Karachi, ,1972 M.Sc. , Middle East Technical University, Ankara, 1975' A D issertation Submitted to the Faculty of Graduate Studies ' through the Department of Chemistry in Partial Fulfillm ent of the Requirements fo r’the Degree of. Do'ctor of Philosophy a t The "University of Windsor W indsorOntario, Canada 1979 © Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. This dissertation has been examined and approved by - Dr. D.S. Tuck ---------------1 / Dr. J.E. Drake < U !. Dr. B.R. McGarvey Dr. J.W. McConkey Dt^vJ. Oliver Wayne/ State University 4 it, Michigan, U.S.A. (External Examiner) X r \ / _ _________________ Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ACKNOWLEDGEMENT The investigations described in this dissertation were carried out in the Department of Chemistry of the University of Windsor, Ontario, Canada between 1975 and 1979 under the supervision of Dr. D. G. Tuck. To him I would like to express my utmost gratitude, for his tremendous help, guidance and encouragement_^£hroughout the research. His drive and boun^l^ss enthusiasm w ill always remain a source of inspiration for me. I would also like to acknowledge the warmth and the invaluable mutual support of my colleagues, in particular Dr. R. Steevensz, Dr. F. Said, Dr. J. Habeeb, L. Victoriano. and S. Zhandire. Their helpful discussions and stimulating companionship made these years a most rewarding and delightful experience. To my parents and elder brother, I owe special gratitude, for even though they were far away, their concern and moral support have always provided the meaning and purpose to my endeavours. I also thank the technical staff and the secretaries of the Department of Chemistry for their valuable assistance and cooperation. At the same tim e, my thanks are also due to Mrs. Joyce Popovich of the Faculty of Law for her patience in typing this manuscript, the quality of~which~''speaks for i t s e l f . i i i Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Finally, I shall take this opportunity to acknowledge the invaluable financial assistance provided by the National Research Council of Canada and the University of Windsor, ■ without which it would have been difficult indeed to coup let e t h i s w o rk . Windsor, Ontario September, 1979 i v Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ABSTRACT A review of the electrochemical synthesis in non-aqueous •media involving main group metals and the transition metals as the^acrificial electrode (cathode or anode) 'is presented. Electrochemical insertion reactions were successfully investigated and a range of neutral and anionic organo- m etallic compounds synthesised 'by sacrificial dissolution ‘of anode metal in non-aqueous media. The products have been identified using physicochemical means. The'possible reaction mechanism of these direct electrochemical reactions by measuring the current efficiency of .the system, and the advantages of electrochemical preparative methods, are also d is c u s s e d . X. Synthesis of neutral organocadmiurn halides . The electrochemical oxidation of cadmium metal in the presence of alkyl or aryl halides leads to the formation of unstable RCdX (where R = Me, Et, n-Bu, CF^ > C^F^'and X - Br, Cl, I). These compounds are•stabilized by either mono or bidentate neutral ligands; these adducts are formed ■ t in good yield. II. Synthesis of anionic organocadmlum dihalxdes Direct electrochemical synthesis gave rise to a series of previously unknown salts or anions, such as RCcD^ (where R = Me, Et, n-Bu, t-Bu, CF^, CgF^; X = Cl, Br, I ) , by the oxidation of cadmium (anode) in a chemical cell in which the v * Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. solution phase was a methanol/benzene mixture, containing the appropriate tetra-n-propylammonium. halide and alkyl * halide. Gram quantities of product were obtained at or near * room temperature.- In general the .compounds hydrolysed and_ decomposed’on exposure' to. air or m oisture. I I I . ' Synthesis of LCdBr, LpCd, LCdMe and LCdPh (L = o-bromo-N,N-dimethylbenzylamine) Oxidative insertion of cadmium metal in between carbon- bromine bond of o-bromo-N ,N-dime thy lbenzylamine was carried out by the electrolysis of o-bromo-N ,N-dimethylbenzylamine in an acetonitrile/benzene mixture and a few mg of Et^NClO^. The sacrificial anode was cadmium, the cathode was tungsten, and all reactions were carried out in a dry nitrogen at­ mosphere. The insertion product LCdBr.so obtained was successfully utilized to prepare LCdMe and LCdPh quanti- * tatively by reaction with MeLi and PhLi. respectively. .Four coordinate bis 2-[Cdime thy lamino)’methyl] phenyl ' cadmium has~heen prepared by the reaction, of 2:1 molar ratio o f 2[Cdimethylamino)methyl phenyl]lithium with anhydrous CdCl2 in diethyl ether.
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