An approach to the synthesis of bridged annulenes
An approach to the synthesis of bridged annulenes
The general development of the chemistry of annulenes is briefly discussed. Various methods for the stabilisation of the conjugated polyene systems are illustrated and the need for efficient general syntheses of bridged annulenes is stressed. The readily available dienediones, 4,8-dimethylbicyclo [3,3,1] nona-3,7-diene-2,6-dione and 4,6-dimethylbicyclo [3,3,1] nona-3,6-diene-2,8-dione, are shown to be important intermediates in the synthesis of novel bridged annulenes. Methods for functionalisation of the methyl groups are described, for example, preparation of polybromo derivatives and products of aldol condensation. Elaboration of the carbonyl groups by Wittig reactions, Reformatsky reactions and Vilsmeier reactions are discussed. Attempts to obtain novel bridged skeletons from these various procedures are analysed, including the preparation of 6,7-benzo5,8-diaza-2,11-dimethyltricyclo 17,212,04,13J trideca-2,4,8,10tetraene from the condensation of o-phenylenediamine and 4,6dimethylbicyclo [3,3,1] nona-3,6-diene-2,6-dione.
University of Southampton
1979
Rawlins, Micheal Frank
(1979)
An approach to the synthesis of bridged annulenes.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The general development of the chemistry of annulenes is briefly discussed. Various methods for the stabilisation of the conjugated polyene systems are illustrated and the need for efficient general syntheses of bridged annulenes is stressed. The readily available dienediones, 4,8-dimethylbicyclo [3,3,1] nona-3,7-diene-2,6-dione and 4,6-dimethylbicyclo [3,3,1] nona-3,6-diene-2,8-dione, are shown to be important intermediates in the synthesis of novel bridged annulenes. Methods for functionalisation of the methyl groups are described, for example, preparation of polybromo derivatives and products of aldol condensation. Elaboration of the carbonyl groups by Wittig reactions, Reformatsky reactions and Vilsmeier reactions are discussed. Attempts to obtain novel bridged skeletons from these various procedures are analysed, including the preparation of 6,7-benzo5,8-diaza-2,11-dimethyltricyclo 17,212,04,13J trideca-2,4,8,10tetraene from the condensation of o-phenylenediamine and 4,6dimethylbicyclo [3,3,1] nona-3,6-diene-2,6-dione.
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Published date: 1979
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Local EPrints ID: 462404
URI: http://eprints.soton.ac.uk/id/eprint/462404
PURE UUID: d0b8b7f7-a2c9-4135-b6f1-374fb6c74751
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Date deposited: 04 Jul 2022 19:07
Last modified: 04 Jul 2022 19:07
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Author:
Micheal Frank Rawlins
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