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Gold-catalysed cycloisomerisations of ketoalkynes

Detty-Mambo, Christelle (2011)
Ph.D. thesis, University of Birmingham.

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The direct cyclisation between alkynes and ketones was described by Conia in 1964. Under high temperatures (150-650 °C), alkynyl and alkenyl ketones were converted into carbocycles, bis-fused carbocycles and spiro compounds by a pericyclic ene-type reaction. However, the use of elevated temperatures limits its applications to thermally robust molecules. Since the original report, a significant amount of effort has been made to develop alternative approaches under mild conditions. These methods employ activated methylenes, frozen enol equivalents or enamine intermediates as nucleophiles in the presence of a Lewis acid (Hg, W, Pt, Au) to activate the unsaturated moiety. Although, synthetically useful, these processes are limited by the necessity to use a preformed enol or a co-catalyst, which involves additional synthetic steps and reagents.

Type of Work:Ph.D. thesis.
Supervisor(s):Davies, Paul
School/Faculty:Colleges (2008 onwards) > College of Engineering & Physical Sciences
Department:School of Chemistry
Subjects:QD Chemistry
Institution:University of Birmingham
ID Code:1740
This unpublished thesis/dissertation is copyright of the author and/or third parties. The intellectual property rights of the author or third parties in respect of this work are as defined by The Copyright Designs and Patents Act 1988 or as modified by any successor legislation. Any use made of information contained in this thesis/dissertation must be in accordance with that legislation and must be properly acknowledged. Further distribution or reproduction in any format is prohibited without the permission of the copyright holder.
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