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Orbital Control and Selectivity in Addition Reactions Orbital Control and Selectivity in Addition Reactions A thesis submitted in partial fulfilment of the requirements for the Degree of Doctor of Philosophy in Chemistry. in the University of Canterbury. by Dugald Quentin McDonald -;;/ University of Canterbury 1991. PHYSICAC SCIENCES LIBRARY THESIS Contents Abstract........................................................................................................................ l Part I 1. The Application of Molecular Orbital Theory to the Diels-Alder Reaction............. S 2. Semi-empirical Molecular Orbital Methods ........................................................ 27 3. Diastereofacial Selectivity in the Diels-Alder Reaction ..................................... 51 Part II 4. The Application of Molecular Mechanics to Investigate Steric Influences in Determining Facial Selectivity ........................................................................... 87 5. Diastereofacial Selection in Diels-Alder reactions to a Cage Diol.. ....................... 97 6. Diastereofacial Selection in Diels-Alder Reactions of Mono and Dimethylidene Substituted Cage Dienes ...................................................................................... lOS 7. Synthetic Studies on Cage Compounds .................................................................. 115 Part III 8. The Application of Semi-empirical Methods to the Study of Reaction Pathways.127 9. AMl and PM3 Studies of the Diels-Alder Reactions of Acetylene ........................133 10. AMl Calculations of Acetylene Additions to Cage-fused Dienes .......................... 147 11. Orbital Mixing in Cage-fused Dienes and the Consequences for Diastereofacial Selection in Diels-Alder Reactions ............................................ 157 12. Cycloaddition Reactions of Diimide ................................................................... 169 13. The "Cieplak" Effect. Direction of Reaction at Facially Dissymmetric 1t Systems by Hyperconjugative Interactions ........................................................ l85 Experimental ........................................................................................................... 197 Crystallography ....................................................................................................... 217 Computer Software ................................................................................................ 227 References ................................................................................................................ 257 Acknowledgments ................................................................................................. 269 1 Abstract. Several topics which are relevant to the results and methods in this thesis are examined in Part I. Recent developments in the application of molecular orbital theory to the Diels-Alder reaction and the history and development of semi-empirical molecular orbital methods are reviewed. A survey of the major developments in understanding diastereofacial selection in the Diels-Alder reaction is also included in Part I. In Part II experimental and molecular mechanics studies are described for the addition of several azo, acetylenic and alkene dienophiles with four cage-fused dienes. Reactions of a dihydroxy substituted cage diene were found to proceed with complete selectivity for reaction from the face of the diene anti to the cyclobutane group, with the exception of the reaction of nitrosobenzene which was determined to be reversible. For most of the dienophiles, however, molecular mechanics calculations of the products in the reactions confirm that the relative stability of the adducts does not control the diastereofacial selection in the reaction. With a series of mono- and dimethylidene substituted cage-fused dienes, reactions of alkene dienophiles showed a strong preference for reaction from the anti face of the diene and this is successfully rationalized by a transition state model based on molecular mechanics. A series of mono and dimethylidene substituted cage dienes showed an opposing trend in facial selectivity, upon reaction with acetylenic dienophiles, to that observed with azo dienophiles. The selectivity observed for the reactions of acetylenic dienophiles cannot be rationalised by the "steric only" molecular mechanics based transition state models and this is interpreted as pointing to the importance of direct interactions between the substituents on the cage diene and the approaching dienophile. Several studies on the chemistry of cage-fused dienes are described with emphasis on the importance of transannular interaction during attempts to effect functional group interconversions of the cage substituents. Part III of this thesis reports studies using the AM1 and PM3 molecular orbital methods to examine several systems where orbital control may be important in determining facial selection. The reaction of acetylene with both simple dienes and cage-fused dienes is 2 examined by application of the AM1 and PM3 methods. The reactions of acetylene with all the dienes studied are predicted to occur in reactions which are both concerted and synchronous. A detailed analysis of the energy changes in the molecular orbital energy levels during the reactions revealed destabilizing interactions involving the "orthogonal" HOMO of acetylenic dienophiles. These are important in determining the diastereofacial selection of reactions of acetylenic dienophiles with cage-fused dienes when there are suitably placed lone pairs on terminal substituents. The extent of CJ I 1t interaction, determined by AM1 calculations for several cage-fused dienes, is shown to vary considerably with the nature of the cage substituents, but this is not considered to be an important factor in determining facial selection. As a model for substituted azo dienophiles, the Diels-Alder reactions of diimide (N2H2) have been studied by the PM3 method. This reaction is predicted to be both concerted and synchronous for the reaction of Z-diimide and butadiene in the exo mode but for the reaction of Z-diimide in the endo mode, the reaction is predicted to proceed via an unsymmetrical transition structure although still in a concerted reaction. The reaction of E-diimide with butadiene is considerably more complicated and three stationary points were located on the potential energy surface. The energy of aziridinium imide intermediates in possible two-step reactions of diimide and butadiene were evaluated by the PM3 method and determined to be approximately the same as the energy of the transition structures in the concerted reactions and so this precludes the involvement of these species in the reaction pathway. Finally the AM1 method was applied to examine the effect of substituents in determining the facial selection in the addition of methanol to 2,3- disubstituted-7-norbomanones and of ethylene to 5-substituted cyclopentadienes. Both of these systems have been proposed to show diastereofacial selection influenced by hyperconjugative stabilization. However, the AM1 method was not able to reproduce the observed facial selection in these reactions. The operation and function of several computer programs developed during the course work for the graphical analysis of the results of molecular mechanics and molecular orbital calculations and for quantifying CJ/rc interaction in dienes are described in the appendix. 3 Part I. Introduction. 1. The Application of Molecular Orbital Theory to the Diels-Alder Reaction. A review of the major applications of variational and perturbational molecular orbital theory to understanding the mechanism and stereochemistry of the Diels-Alder reaction. 2. Semi-empirical Molecular Orbital Methods. The history and theoretical basis of modern semi-empirical molecular orbital methods. 3. Diastereofacial Selectivity in the Diels-Alder Reaction. A review of the Diels-Alder reactions of facially dissymmetric dienes and dienophiles with particular emphasis on the steric and electronic interactions which have been proposed to be important in determining diastereofacial selectivity. 5 Chapter 1. The Application of Molecular Orbital Theory to the Diels-Alder Reaction. In the time since the [1t2 + n;4] cycloaddition was first reportedl by Diels and Alder in · 1928, this reaction has been of considerable interest to synthetic organic chemists. This interest has not diminished in recent years; an examination of the number of abstracts listed with the Chemical Abstracts service which list the words "Diels-Alder" in the period 1967- 1990 shows that the number of such references has at least kept pace with the total number of articles abstracted (Figure 1). 1500 Figure 1. Chemical Abstracts Entries for "Diels-Alder" Ill G) ·;,:: in two yearly intervals 1967-1990 ~ 1000 0 -... G) ..CI E 500 z::1 0 67-68 69-70 71-72 73-74 75-76 77-78 79-80 81-82 83-84 85-86 87-88 89-90 Year In addition to having tremendous synthetic utility, the apparent simplicity of the reaction, the fact that it is little influenced by external effects such as solvent, and the desire to understand and therefore gain greater control over the application of this reaction has been the impetus for a large volume of research into the mechanism. Because the limitations of experimental methods for elucidating the mechanism quickly became apparent, molecular orbital theory, in both quantitative and semi-quantitative forms, has played a vital role in developing an understanding, not only of the mechanism of the reaction but also of the regiochemistry.
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