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Some aspects of the chemistry of benzobicyclo systems

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thesis
posted on 31.10.2018, 15:00 by John H. Hollinshead
The rearrangement reactions of 1-methoxybenzobicyclo-[2,2,2]-octatriene derivatives in strong acid have been studied. In particular 1-methoxytetrafluoro-, 1-methoxytetrachloro-, and 1-methoxybenzobarrelene have been prepared labelled with 14C at C-4. Rearrangement of these compounds, in strong acid, leads in each case, to three isomeric ketones. The major product in each rearrangement was the corresponding benzobarrelenone, formed, in each case, by two distinct pathways. The 14C label in each benzobarrelenone was scrambled between C-4 and C-5 as a result of the two different mechanisms. A suitable degradation procedure has been devised which allows the 14C activity in C-4 and C-5 of each ketone to be determined, and hence an evaluation of the percentage rearrangement which proceeds by the two mechanistic pathways previously suggested. [Continues.]

Funding

Science Research Council.

History

School

  • Science

Department

  • Chemistry

Publisher

© John Henry Hollinshead

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

1978

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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