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Studies in the chemistry of halogenated benzynes

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thesis
posted on 19.09.2018, 09:03 by Barry Hankinson
Chapter 1 deals with the principal methods for the generation of arynes and reviews briefly some of the properties of these reactive intermediates. Chapter 2 deals with the reactions of tetrafluorobenzyne generated from pentafluorophenyl magnesium chloride or pentafluorophenyl lithium with anisole, phenetole, p-cresol methyl ether, the 3 isomeric dimethoxybenzenes, symmetrical trimethoxybenzene 2,6-dimethoxytoluene, 1-methoxy-5,6,7,8-tetrafluoronaphthalene and N,N-dimethyl-p-toluidine. The pyrolysis and photolysis of some of the adducts are discussed. Ketonic adducts have been shown to eliminate ketenes. Chapter 3 investigates the reactions of tetrafluorobenzyne with 2-methyl, 2,5-dimethyl and 2-methyl-5-tert-butylfurans. Attempts to prepare anthracenes by elaboration of the adducts with butadiene are discussed. Chapter 4 studies the reactions of benzynes with various polycyclic hydrocarbons (namely fulvenes, phenanthrene, methanocyclodecapentaene, acenaphthene and acenaphthylene). The reaction of tetrafluorobenzyne with dimethyl fulvene yields interesting 2-to-1 adducts. Chapter 5 deals with the PMR spectral data of most of the adducts reported in Chapters 2, 3 and 4. Several ABX spectra have been calculated and compared with the observed spectra.

Funding

Loughborough University. Hickson and Welsh Ltd.

History

School

  • Science

Department

  • Chemistry

Publisher

© B. Hankinson

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

1970

Notes

A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.

Language

en

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