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An Inquiry Into the Nature and Mechanism of Addition of Organocadmium Reagents to Simple Carbonyl Compounds

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An Inquiry Into the Nature and Mechanism of Addition of Organocadmium Reagents to Simple Carbonyl Compounds University of New Hampshire University of New Hampshire Scholars' Repository Doctoral Dissertations Student Scholarship Spring 1969 AN INQUIRY INTO THE NATURE AND MECHANISM OF ADDITION OF ORGANOCADMIUM REAGENTS TO SIMPLE CARBONYL COMPOUNDS WILLIAM J. KAUFFMAN Follow this and additional works at: https://scholars.unh.edu/dissertation Recommended Citation KAUFFMAN, WILLIAM J., "AN INQUIRY INTO THE NATURE AND MECHANISM OF ADDITION OF ORGANOCADMIUM REAGENTS TO SIMPLE CARBONYL COMPOUNDS" (1969). Doctoral Dissertations. 901. https://scholars.unh.edu/dissertation/901 This Dissertation is brought to you for free and open access by the Student Scholarship at University of New Hampshire Scholars' Repository. It has been accepted for inclusion in Doctoral Dissertations by an authorized administrator of University of New Hampshire Scholars' Repository. For more information, please contact [email protected]. This dissertation has been 70-2082 microfilmed exactly as received KAUFFMAN, William J., 1945- AN INQUIRY INTO THE NATURE AND MECHANISM OF ADDITION OF ORGANO- CADMIUM REAGENTS TO SIMPLE CARBONYL COMPOUNDS. University of New Hampshire, Ph.D., 1969 Chemistry, organic University Microfilms, Inc., Ann Arbor, Michigan Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. AN INQUIRY INTO THE NATURE AND MECHANISM OF ADDITION OF ORGANOCADMIUM REAGENTS TO SIMPLE CARBONYL COMPOUNDS by WILLIAM J . KAUFFMAN B.S., Juniata College, 1966 A THESIS Submitted to the University of New Hampshire In Partial Fulfillment of The Requirements for the Degree of Doctor of Philosophy Graduate School Department of Chemistry May, 1969 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. This thesis has been examined and approved. (JQ a aX' Dr. Paul R. JoneGs, T hesis D irecto r Professor of Chemistry ^9 -- W aatyyw x*— DrV. James D. Morrison Associate Professor of Chemistry fC- ___________ Dr. Kenneth K. Andersen Associate Professor of Chemistry f b Dr. Jafiies H. Weber Associate Professor of Chemistry Dr. Philip J K & £w yex v Associate Professor of Zoology T f W , . 3 ^ D ate ff Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ACKNOWLEDGMENT The author wishes to express his sincere apprecia­ tion to Dr. Paul R. Jones for his assistance, patience and understanding during the course of this investigation and the preparation of this manuscript. Special recognition is due Edwin J. Goller, whose valuable comments and collaboration have been most beneficial. Final appreciation is due to the National Science Foundation for the financial support given during this investigation. 111• • • Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. TABLE OF CONTENTS LIST OF TABLES . ......................... v i i i ABSTRACT........................................................................................................... i x INTRODUCTION................................................................................................. 1 HISTORICAL BACKGROUND......................................................................... 2 EXPERIMENTAL............................... ................................................................. 20 Instrumentation ....................................................... ..... 20 M a t e r i a l s ............................................................................................ 20 Experimental Apparatus .......................................................... 21 Reaction of Filtered, in situ, Diethylcadmium (Br,Cl) with Benzoyl Chloride ............................................ 22 Reaction of in situ Diethylcadmium (prepared from Diethylmagnesium) with Benzoyl Chloride . 23 Reaction of Filtered, in situ Diethylcadmium with Benzoyl Chloride in Ether ....................................... 24 Reaction of Diethylcadmium (one step) with Benzaldehyde in E ther ............................................................... 25 Reaction of Diethylcadmium (one step) with Benzaldehyde in THF ....................... 26 Reaction of Centrifuged, in situ Diethylcadmium (Br,Cl) with Benzaldehyde in E th e r ............................. 26 A. S u p e r n a t a n t ............................................................... 26 B. R e s i d u e ......................................................................... 27 Reaction of in situ Diethylcadmium (Br,Cl) with Benzaldehyde in Ether ............................................................... 28 Reaction of in situ Dimethylcadmium (I,Cl) with £-Nitroacetophenone in E th e r .................................. 28 iv Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Reaction of in situ Diethylcadmium (Br,Cl) with m-Nitrobenzaldehyde in Ether ................................................. 29 Reaction of in situ Diethylcadmium (Br,Cl) with Cyclohexanone .................................................................................. 30 Reaction of in situ Diethylcadmium (I, Cl) with Cyclohexanone .................................................................................. 31 Reaction of Ethylcadmium Halide (I,Cl) with Cyclohexanone .................................................................................. 31 Reaction of in situ Dimethyl cadmium (I, Cl) with Cyclohexanone ......................................................................... 32 Reaction of Methylcyclohexoxycadmium (I,Cl) with Cyclohexanone ................................................•........................ 33 Reaction of in situ Dimethylcadmium (I,Cl) with Acetophenone ....................... 34 Reaction of In situ Di-n-propylcadmium (Br,Br) with H eptanal.................................................................... 34 Reaction of n-Propylcadmium Bromide with H ep tan al .................................................................... ...... 35 Reaction of Phenylmagnesium Bromide with 2-Phenylpropanal ....................................................................35 Reaction of in situ Diphenylcadmium (Br,Cl) with 2-Phenylpropanal............................................................... 3fa Preparation of Anhydrous Magnesium Iodide .... 44 Preparation of Anhydrous Magnesium Bromide .... 44 Reaction of Methylmagnesium Bromide and Iodide with 4-t:-Butylcyclohexanone ................................... 44 Preparation and Analysis of "Purified" Dimethylcadmium ........................................................... 45 Reaction of "Reconstituted" Dimethylcadmium with 4-jt-Butylclohexanone ........................ 45 Reaction of 4-JL-Butylcyclohexanone*MgX 2 w ith "Purified" Dimethylcadmium ..................................................... 46 Reaction of in situ Dimethylcadmium with 4-_t- Butylcyclohexanone in Ether .................... 47 v Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Reaction of in situ Dimethylcadmium (Br,I) with 4-t:-B utylcyclohexanone in T H F ............................................ 48 GLPC Analysis of the Reaction Mixtures from in situ Dimethylcadmium with 4-t-Butylcyclo- h e x a n o n e ............................................................................................ 49 Control Experiments for the in situ Dimethylcadmium reactions with 4-t:- Butylcyclohexanone ..... ............................................ 50 Reaction of in situ Di-n-propylcadmium with 4-_t-Butylcyclohexanone in E th e r ....................................... 51 Reaction of n-Propylmagnesium Iodide with 4-_t- Butylcyclohexanone in Ether ..... ........................ 52 Trimethylamine Borane Reduction of 4-1:- Butylcyclohexanone .................................................................... 52 Separation of cis-(axial)-and trans-(equatorial)- 4-t^-Butylcyclohexanols .......................................................... 53 GLPC Analysis of the Reaction Mixture from Di-n-propylcadmium and 4-t^-Butylcyclohexanone . 53 Attempted Equilibration of cis-(axial)-4-t- Butylcyclohexanol ......................................................................... 55 Attempted Equilibration of trans-(equatorial)-4- t-Butylcyclohexanol .................................................................... 57 Reaction of in situ Dimethylcadmium with 2-Phenylpropanal .............................................................. 57 Reaction of Methylmagnesium Iodide with 2-Phenylpropanal 58 GLPC Analysis of the Reaction Mixture from Dimethylcadmium and 2-Phenylpropanal ........................ 60 Isolation of three-3-Phenyl-2-butanol ........................ 61 Isolation of erythro-3-Phenyl-2-butanol .................... 62 Attempted Equilibration of erythro-3-Phenyl-2- b u tan o l ............................................................................................ 63 Attempted Equilibration of threo-3-Phenyl-2- b u t a n o l .............................................................. 64 Preparation of 2-Phenylbutyryl Chloride .................... _ 65 Preparation of Imidazolide of 2-Phenylbutyric a c id ....................... 65 v i Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Preparation of 2-Phenylbutanal ............................................ 66 Reaction of Methylmagnesium Bromide with 2-Phenylbutanal .............................................................................
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