Radical cyclisations of methylenecyclopropane deratives
Radical cyclisations of methylenecyclopropane deratives
This thesis was concerned with the synthesis, and radical cyclisations, of compounds containing a methylenecyclopropane moiety. Special interest is given to developing tandem radical cyclisations to create polycyclic systems.
Chapter 1 describes the syntheses of suitable 1,2-disubstituted methylenecyclopropane derivatives, and the investigations into their tandem cyclisations. Tandem cyclisation of (39), to give (40), was found to be a particularly clean and efficient reaction, when slow addition techniques were used for the addition of tin hydride and AIBN. (Fig. 8997A)
Chapter 2 describes the syntheses of 1,2-disubstituted methylenecyclopropylmalonyl compounds suitable for atom transfer mediated cyclisations, (42). Under atom transfer conditions these compounds underwent the anticipated 7-endo cyclisation to give (43). However, the desired tandem cyclisation, to give radical (44), did not occur and cyclopropyl radical (43) was trapped by iodine atom transfer. (Fig. 8997B)
University of Southampton
1997
Pike, Kurt Gordon
(1997)
Radical cyclisations of methylenecyclopropane deratives.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
This thesis was concerned with the synthesis, and radical cyclisations, of compounds containing a methylenecyclopropane moiety. Special interest is given to developing tandem radical cyclisations to create polycyclic systems.
Chapter 1 describes the syntheses of suitable 1,2-disubstituted methylenecyclopropane derivatives, and the investigations into their tandem cyclisations. Tandem cyclisation of (39), to give (40), was found to be a particularly clean and efficient reaction, when slow addition techniques were used for the addition of tin hydride and AIBN. (Fig. 8997A)
Chapter 2 describes the syntheses of 1,2-disubstituted methylenecyclopropylmalonyl compounds suitable for atom transfer mediated cyclisations, (42). Under atom transfer conditions these compounds underwent the anticipated 7-endo cyclisation to give (43). However, the desired tandem cyclisation, to give radical (44), did not occur and cyclopropyl radical (43) was trapped by iodine atom transfer. (Fig. 8997B)
This record has no associated files available for download.
More information
Published date: 1997
Identifiers
Local EPrints ID: 463050
URI: http://eprints.soton.ac.uk/id/eprint/463050
PURE UUID: f2154f34-5ac0-4bda-a62a-3820905818b1
Catalogue record
Date deposited: 04 Jul 2022 20:41
Last modified: 04 Jul 2022 20:41
Export record
Contributors
Author:
Kurt Gordon Pike
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