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Title: The reactivity of hindered amides
Author: Totterdell, Laura E.
ISNI:       0000 0004 5923 6843
Awarding Body: University of Bristol
Current Institution: University of Bristol
Date of Award: 2015
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The reactivity of a new class of hindered amides has been investigated. These amides have been found to undergo facile nucleophilic substitution reactions with a range of nucleophiles. The enhanced reactivity of these compounds, described as "rotamides", is attributed to an exceptionally low barrier to C-N bond rotation, as a result of their sterically hindered structures. This thesis describes the studies undeliaken to elucidate the reaction mechanism. The case for the previously proposed proton switchlketene mechanism has been strengthened by a kinetics study into the nucleophilic substitution reaction of a highly reactive rotamide with butanol. Ketene trapping experiments have also provided strong evidence to support the existence of the ketene intermediate suggested by the proposed proton switch/ketene mechanism.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available