Thesis-1970-Hankinson.pdf (2.71 MB)
Download fileStudies in the chemistry of halogenated benzynes
thesis
posted on 19.09.2018, 09:03 authored by Barry HankinsonChapter 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