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Model systems for the study of carbocation-π interaction.

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Call No.	QD305.C3 P67 2001
Author	Popovici-Müller, Janeta V.
Title	Model systems for the study of carbocation-π interaction.
Date	2001
Abstract	Interaction with aromatic π systems has become recognized as an important mode of stabilization of carbocation intermediates in biological reactions. To gain insight into such carbocation-π interactions, we have undertaken a study of intramolecular model systems, one being a benzobicyclo[4.2.1]nonene model system. Our goal is to compare, for example, the stabilities of a syn carbocation, in which π complexation is possible, vs. an isomeric anti carbocation, in which π complexation is precluded. Syntheses of alkenes as carbocation precursors, and the results of the NMR studies of the kinetics of protonation of these alkene precursors will be presented. Computational results for the optimized geometries and relative energies of alkenes and carbocations will be discussed to explain the experimental data. In another model system that was proposed for investigation, a benzobicyclo[3.2.1]octenyl ketone was needed as an important intermediate for the synthesis of the corresponding model system. Attempts to develop an efficient synthesis that would provide gram quantities of this intermediate ketone will be presented in this thesis. Finally, during the synthesis of a naphthalene diol needed for the synthesis of a naphthalene bridged model system, initially proposed for the study of carbocation-π interaction, a novel benzonorcaradiene derivative was discovered in the lithium aluminum hydride reduction of 1,8-naphthalic anhydride. Experiments designed to elucidate the mechanism of the benzonorcaradiene formation, and results of deuterium labeling experiments and molecular modeling will be discussed in this thesis.
Description	1 online resource (xv, 218 leaves) : illustrations
Format	application/pdf
Advisor	Spencer, Thomas A., Jr.
Subject	Carbocations -- Reactivity. ; Aromatic compounds -- Reactivity.
College	Dartmouth College -- Department of Chemistry.
Issuing Body	Dartmouth Dissertations are made available through the Dartmouth Digital Library.
Degree	Thesis (Ph.D)--Dartmouth College.
Copyright	In Copyright. This material is protected by copyright and/or related rights. You are free to use this material in any way that is permitted by copyright law that applies to your use. For other uses, you need to obtain permission from the rights-holder(s). http://rightsstatements.org/page/InC/1.0/
DOI	https://doi.org/10.1349/ddlp.2864

Title	popovici2001 1
Full Text	M odel System s for the Study o f Carbocation-7[ Interaction A Thesis Submitted to the Faculty in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry by Janeta V. Popovici-Muller DARTMOUTH COLLEGE Hanover. New Hampshire May 31. 2001 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission.

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Model systems for the study of carbocation-π interaction.

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Model systems for the study of carbocation-π interaction.

Model systems for the study of carbocation-π interaction.