Pryke, James A (2012) Novel strategies for the construction of cyclic boronate esters and acids & novel aspects of furan chemistry. Doctoral thesis (DPhil), University of Sussex.

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Abstract

Methodology studies for cyclic boronate ester synthesis

Figure i: Target molecules (see Abstract in pdf for image)

Structures i,ii,iii represent a general depiction of cyclic boron-containing heterocyles
targeted in this methodology study. These molecules will be made using a range of
new organic pathways. A 1,3 nitrogen-boron relationship in selected structures will
also be investigated due to its importance in pharmaceutical chemistry.
In the pursuit of cyclic boranes a new method for the preparation of unsaturated
ketones has been discovered, which utilises the boron chemistry outlined below.

Figure ii: Reagents and Conditions: (a) tBuLi, B(OIPr)3, Et2O, -79 °C, 20 % (see Abstract in pdf for image)

Novel aspects of furan chemistry
It was found that the furan derivative vii, when treated with palladium salts, gave the
bis-annulated benzene structure viii. This sequence gave rise to a novel method for
the construction of aromatic rings. This reaction was tested on a range of substituted
furans in order to examine the scope of this reaction.

Figure iii: Reagents and Conditions: (a) Pd(OAc)2, K2CO3, MeCN, 80 °C, 25% (see Abstract in pdf for image)

Item Type:	Thesis (Doctoral)
Schools and Departments:	School of Life Sciences > Chemistry
Subjects:	Q Science > QD Chemistry > QD0241 Organic chemistry
Depositing User:	Library Cataloguing
Date Deposited:	19 Jun 2012 14:02
Last Modified:	25 Aug 2015 15:16
URI:	http://sro.sussex.ac.uk/id/eprint/39633

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