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Durham e-Theses
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The synthesis and reactions of novel butadiyne derivatives

West, Kara (2007) The synthesis and reactions of novel butadiyne derivatives. Doctoral thesis, Durham University.



The synthesis, isolation and characterisation of aryl and heteroarylbutadiynes is herein reported. X-ray structural analysis for terminal butadiynes 72,118, 143, 157, 162 and 172 has been obtained. The packing diagrams indicate, in most cases, a hydrogen bonding interaction between the terminal acetylenie proton and the appropriate atom in the ring. An important feature of our synthetic methodology is the use of the 2-hydroxy-2-propyl protecting group, which facilitates purification from protected species, due to a large difference in polarity. The synthesis of mono- and di-deprotected bis-butadiynes is also reported; indeed X- ray structural analysis of di-deprotected pyridyl bis-butadiyne 234 has been obtained, as shown in the figure below The reactions of aryl and heteorarylbutadiynes and bis-butadiynes have also been investigated, leading to the synthesis of molecular-wire precursors 262 and 264.

Item Type:Thesis (Doctoral)
Award:Doctor of Philosophy
Thesis Date:2007
Copyright:Copyright of this thesis is held by the author
Deposited On:08 Sep 2011 18:29

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