Stereoselective synthesis through the activation of small rings

This thesis describes the use of both, a carbanion Payne-type rearrangement and η4-dienyl and η5-pentadienyl iron tricarbonyl complexes in organic chemistry. A carbanion Payne-type rearrangement has been developed and its reactivity investigated, with the subsequent trapping of a series of aldehydes...

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Bibliographic Details
Main Author: Cummins, Jaime
Published: Loughborough University 2006
Subjects:
Online Access:https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.432198
Description
Summary:This thesis describes the use of both, a carbanion Payne-type rearrangement and η4-dienyl and η5-pentadienyl iron tricarbonyl complexes in organic chemistry. A carbanion Payne-type rearrangement has been developed and its reactivity investigated, with the subsequent trapping of a series of aldehydes or imines. The results are disappointing with no desired tetrahydrofuran-, tetrahydropyran- or pyrrolidine-containing molecules synthesised, although reasons for this are discussed. A novel 1,3-dipole containing a η5-iron tricarbonyl pentadienyl complex was synthesised on opening of a cyclopropane, subsequently trapping with a series of aldehyde and imines to efficiently form tetrahydrofuran and pyrrolidine ring structures, respectively.