Thesis-1971-McCarty.pdf (3.43 MB)
Some novel aspects of the synthesis of oxygen heterocycles
thesis
posted on 2018-10-18, 08:38 authored by C.T. McCartyThe reactions of benzyne and tetrachlorobenzyne with αβ-unsaturated aldehydes which form 2-H-chromen derivatives have been investigated. The mechanism was established by [14C] and [2H] labelling experiments and proceeds initially through a benzoxeten intermediate. Subsequent opening of these intermediates followed by thermal cyclisation of an o-quinone methide gave the products. A degradation of 5,6,7,8-tetrachloro-2-H-flaven to a tetrachlorosalicylic acid derivative was carried out, to confirm the position of the [14C] radiolabel. Also described are a number of rearrangement reactions of 5,6,7,8-tetrachloro-4-H-flaven in which 2-benzoyl-dihydrobenzofuran, or 2-benzoyl-benzofuran derivatives were obtained if bromine was present in the reaction mixture. [Continues.]
Funding
Science Research Council (research studentship).
History
School
- Science
Department
- Chemistry
Publisher
© C.T. McCartyPublisher 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
1971Notes
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.Language
- en