The synthesis of novel C2 chiral diamine ligands
The synthesis of novel C2 chiral diamine ligands
This thesis reviews the history and development of C2 chiral diamine ligands and a comprehensive list has been compiled. The synthesis and use of representative examples from this list have been illustrated.
Earlier work has shown that iminium ions derived from aromatic amines function as electron poor 2-ara-1,3-butadiene equivalents and will participate in [4+2] cycloaddition reactions with alkenes resulting in the formation of a chiral compound with a C2 axis of symmetry. This reaction is reviewed and is the basis for part of the work described in this thesis, involving the synthesis of novel C2 chiral diamine ligands from 1,2-phenyenediamines and diaminoacenaphthene derivatives. A series of interesting side products from the reaction of various 1,2-phenylenediamines with cyclopentadiene has been the synthesis of a number of benzodiazepines which have been isolated and characterised.
The synthesis of a new class of fluorescent N-alkyl-4, 5-(R,R)- and (S, S)-di(α)-methylbenzylamino-1, 8-naphthalimide ligands via the aromatic nucleophilic substitution of suitable acenaphthene precursors with chiral amines is also presented and discussed. The further development of this type of ligand has resulted in the synthesis of a novel series of fluorescent C2 chiral diamine ligands, which may be attached to a polymer resin.
University of Southampton
Mitchell, Preston Lincoln
1994
Mitchell, Preston Lincoln
Mitchell, Preston Lincoln
(1994)
The synthesis of novel C2 chiral diamine ligands.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
This thesis reviews the history and development of C2 chiral diamine ligands and a comprehensive list has been compiled. The synthesis and use of representative examples from this list have been illustrated.
Earlier work has shown that iminium ions derived from aromatic amines function as electron poor 2-ara-1,3-butadiene equivalents and will participate in [4+2] cycloaddition reactions with alkenes resulting in the formation of a chiral compound with a C2 axis of symmetry. This reaction is reviewed and is the basis for part of the work described in this thesis, involving the synthesis of novel C2 chiral diamine ligands from 1,2-phenyenediamines and diaminoacenaphthene derivatives. A series of interesting side products from the reaction of various 1,2-phenylenediamines with cyclopentadiene has been the synthesis of a number of benzodiazepines which have been isolated and characterised.
The synthesis of a new class of fluorescent N-alkyl-4, 5-(R,R)- and (S, S)-di(α)-methylbenzylamino-1, 8-naphthalimide ligands via the aromatic nucleophilic substitution of suitable acenaphthene precursors with chiral amines is also presented and discussed. The further development of this type of ligand has resulted in the synthesis of a novel series of fluorescent C2 chiral diamine ligands, which may be attached to a polymer resin.
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Published date: 1994
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Local EPrints ID: 458632
URI: http://eprints.soton.ac.uk/id/eprint/458632
PURE UUID: eca57022-9f25-4475-af7a-8348db41d4c9
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Date deposited: 04 Jul 2022 16:52
Last modified: 04 Jul 2022 16:52
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Author:
Preston Lincoln Mitchell
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