Lewis acid mediated cyclisations of methylene and alkylidenecyclopropanes
Lewis acid mediated cyclisations of methylene and alkylidenecyclopropanes
This thesis is concerned with the addition or cyclisation of methylene and alkylidenecyclopropanes to C=X bonds mediated by a Lewis acid in the formation of novel heterocyclic compounds. Various intra- and intermolecular processes are reported including additions to aldehydes, ketones and hydrazones.
Chapter 2 describes the intermolecular addition of silyl methylenecyclopropanes to aldehydes affording tetrahydrofurans and furofurans. The effect on the cyclisation of different silyl groups and additional substituents on the methylenecyclopropane was investigated.
Chapter 3 presents the intramolecular cyclisation of methylenecyclopropylimines to give azabicycles. The effect of different silyl groups on the cyclisation of hydrazones was briefly investigated. Particular attention was paid to a mechanistic study of the cyclisation of methylenecyclopropylhydrazones giving azabicycles.
Chapter 4 details the intramolecular cyclisation of alkylidenecyclopropylcarbonyls to yield chloroalkenols and bicyclic ethers. This methodology could be applied to the synthesis of various natural products.
University of Southampton
Patient, Lee
99c26bbc-a794-497a-8c20-5a43bb96de6f
2003
Patient, Lee
99c26bbc-a794-497a-8c20-5a43bb96de6f
Patient, Lee
(2003)
Lewis acid mediated cyclisations of methylene and alkylidenecyclopropanes.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
This thesis is concerned with the addition or cyclisation of methylene and alkylidenecyclopropanes to C=X bonds mediated by a Lewis acid in the formation of novel heterocyclic compounds. Various intra- and intermolecular processes are reported including additions to aldehydes, ketones and hydrazones.
Chapter 2 describes the intermolecular addition of silyl methylenecyclopropanes to aldehydes affording tetrahydrofurans and furofurans. The effect on the cyclisation of different silyl groups and additional substituents on the methylenecyclopropane was investigated.
Chapter 3 presents the intramolecular cyclisation of methylenecyclopropylimines to give azabicycles. The effect of different silyl groups on the cyclisation of hydrazones was briefly investigated. Particular attention was paid to a mechanistic study of the cyclisation of methylenecyclopropylhydrazones giving azabicycles.
Chapter 4 details the intramolecular cyclisation of alkylidenecyclopropylcarbonyls to yield chloroalkenols and bicyclic ethers. This methodology could be applied to the synthesis of various natural products.
Text
922138.pdf
- Version of Record
More information
Published date: 2003
Identifiers
Local EPrints ID: 465163
URI: http://eprints.soton.ac.uk/id/eprint/465163
PURE UUID: cde5ea11-271b-4ef0-8e77-c87a18f569f6
Catalogue record
Date deposited: 05 Jul 2022 00:26
Last modified: 16 Mar 2024 19:59
Export record
Contributors
Author:
Lee Patient
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics