Macrocyclisation of thiophenes via the Mannich reaction

Rooney, P.B., 1997. Macrocyclisation of thiophenes via the Mannich reaction. PhD, Nottingham Trent University.

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A number of 3,4-dialkoxythiophene compounds have been synthesised, and their reactivities assessed by the Mannich reaction with secondary amines. These reactivities are discussed in terms of the degree of steric hindrance of the 2 and 5 positions of the thiophene ring. Attempts also have been made to synthesise bis(3,4-alkoxythiophene) polyethers related to dibenzo-18-crown-6 et al., by the Williamson ether synthesis, however under the conditions reported by this author, the [1+1] cyclisation compound was the major product.

Several bis-[2-(thienyl)methyl] amines derived from 3,4- ethylenedioxythiophene are reported, their syntheses being performed under both normal and high dilution conditions. Each synthesis also afforded the trithienylmethylamine oligomers, as well as polymeric material. Attempts to cyclise the bis-[2-(thienyl)methyl] amines with a further moiety of secondary diamine gave as the major product 2-methyl-3,4-ethylenedioxythiophene-5- carboxaldehyde, arising from a 1,6-Hofmann elimination.

Item Type: Thesis
Creators: Rooney, P.B.
Date: 1997
ISBN: 9781369325010
Divisions: Schools > School of Science and Technology
Record created by: Laura Ward
Date Added: 25 Jun 2021 08:19
Last Modified: 01 Nov 2023 14:38

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