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Title: The chemistry of ynamides and yndiamides
Author: Mansfield, Steven
ISNI:       0000 0004 7971 6940
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2019
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There have been significant developments in both the synthesis and applications of nitrogen-substituted alkynes since the turn of the millennium, but there is still much that remains unexplored. In continuing these developments, two projects have been completed: (i) A general copper-catalysed synthesis of ynamides from 1,2-dichloroenamides was achieved with broad substrate scope. This includes the use of acyclic secondary amides, acyclic ureas and sterically hindered enamide partners. (ii) The first known synthesis of yndiamides was developed, which involves the copper-catalysed coupling of 1,1-dibromoenamides with sulfonamides and phosphoramidates. A preliminary study of yndiamide reactivity in transition metal- and Brønsted acid-catalysed processes was also performed. Combined with the aid of crystallographic, spectroscopic and computational analyses, more fundamental aspects of these compounds have been uncovered during these studies, including conformational preferences. Questions were also raised as to how these preferences can affect the reactivity and stability of ynamides and yndiamides.
Supervisor: Anderson, Edward Sponsor: Engineering and Physical Sciences Research Council
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Chemistry, Organic ; X-ray Crystallography