Study of orbital interactions in saturated organic compounds
Study of orbital interactions in saturated organic compounds
The influence of electronic effects on the stereochemistry of nucleophilic and electrophilic attack on organic substrates is discussed. The role of different spectroscopic techniques in studying long range orbital interactions is analysed, and those conformational requirements for significant interactions described. The reduction of some Ssubstituted ketones and the oxidation and alkylation of some Bsubstituted alkyl sulphides, using bridged rigid substrates have been studied. In the absence of steric factors electronic effects control the stereochemistry of attack. The origin of this control is a distortion of the electron density of the orbitals at the reaction centre. This distortion stems from interaction with adjacent a-orbitals. Photoelectron and ultra-violet spectroscopy have been used to probe electronic interactions in the same series of bridged substrates. Substantial interactions have been observed in B-thiaketones. A correlation between the stereochemical results and the spectroscopic analysis is made.
University of Southampton
1978
Miller, Barry William
(1978)
Study of orbital interactions in saturated organic compounds.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The influence of electronic effects on the stereochemistry of nucleophilic and electrophilic attack on organic substrates is discussed. The role of different spectroscopic techniques in studying long range orbital interactions is analysed, and those conformational requirements for significant interactions described. The reduction of some Ssubstituted ketones and the oxidation and alkylation of some Bsubstituted alkyl sulphides, using bridged rigid substrates have been studied. In the absence of steric factors electronic effects control the stereochemistry of attack. The origin of this control is a distortion of the electron density of the orbitals at the reaction centre. This distortion stems from interaction with adjacent a-orbitals. Photoelectron and ultra-violet spectroscopy have been used to probe electronic interactions in the same series of bridged substrates. Substantial interactions have been observed in B-thiaketones. A correlation between the stereochemical results and the spectroscopic analysis is made.
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Published date: 1978
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Local EPrints ID: 458389
URI: http://eprints.soton.ac.uk/id/eprint/458389
PURE UUID: bdb83d3a-d82a-40b5-aa3d-d9e9b28c95d8
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Date deposited: 04 Jul 2022 16:48
Last modified: 04 Jul 2022 16:48
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Author:
Barry William Miller
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