Synthesis of polysubstituted fatty acids via thiophene intermediates

Gledhill, AP, 1991. Synthesis of polysubstituted fatty acids via thiophene intermediates. PhD, Nottingham Trent University.

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Abstract

This thesis is an Investigation Into the possibility of preparing polysubstituted fatty acids - seco-aclds - via Raney nickel desulphurisation of polysubstituted thiophene Intermediates.

A variety of hydroxythiophene carboxylates were prepared. A number of these were 0-methylated, saponified and either decarboxylated or converted to acid chlorides. Two examples were 0-glycosidated.

Acetoxy - and aryloxy - derivatives of several hydroxythiophene carboxylates were prepared and subjected to Fries rearrangement. The reaction failed in the majority of cases, with cleavage of the ester occurring without subsequent rearrangement. Five esters were successfully Fries rearranged to give thienyl and dithienyl ketones.

A number of polysubstituted thienyl and dithienyl ketones were prepared using Friedel-Crafts acylation.

Raney nickel desulphurisation of thienyl and dithienyl ketones gave seco acids, with only moderate success. The products obtained were found to be impure in the majority of cases. However, one model seco acid was prepared.

A study of the stereoselectlvity of the Raney nickel desulphurisation process with respect to hydroxy groups attached directly to a thiophene ring proved inconclusive.

An investigation into the Raney nickel desulphurisation of thiophenes containing optically active side-chains demonstrated that no racemisation of chiral centres occurs.

Item Type:	Thesis
Creators:	Gledhill, A.P.
Date:	1991
ISBN:	9781369324563
Identifiers:	Number Type PQ10290207 Other
Divisions:	Schools > School of Science and Technology
Record created by:	Linda Sullivan
Date Added:	16 Jun 2021 15:16
Last Modified:	17 Oct 2023 14:12
URI:	https://irep.ntu.ac.uk/id/eprint/43097

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