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The investigation of methylmagnesium chloride as a non-nucleophilic base
Gbadebo, Omolola
The use of methylmagnesium chloride (MeMgCl) as a non-nucleophilic base is explored in this thesis. Grignard reagents react in nucleophilic addition reactions with nitriles yielding a ketone upon work-up, but in the research discussed in this thesis, they are employed in deprotonation alpha to the nitrile resulting in the formation of an anion which can then undergo a SN2 reaction with an alkyl halide. The pharmaceutical company Roche Ireland Ltd developed a new convenient synthetic procedure for the synthesis of 1-(2-ethylbutyl) cyclohexane-1-carbononitrile 2, where MeMgCl plays the role of a non-nucleophilic base when used with catalytic amounts of an amine. The main objective of this thesis was to explore extending the applications of the MeMgCl methodology shown in Scheme 1 by replacing ethylbutyl bromide with other electrophiles and by substituting cyclohexanecarbonitrile with other nitriles and substrates bearing other electron-withdrawing groups.
Keyword(s): Grignard reaction; Nitriles; Alkylation; Magnesium bases; Amides; Chemistry; Science
Publication Date:
Type: Doctoral thesis
Peer-Reviewed: Unknown
Institution: NUI Galway
Publisher(s): NUI Galway
Supervisor(s): O'Leary, Patrick
Smith, Dennis
First Indexed: 2019-03-23 06:44:52 Last Updated: 2019-03-23 06:44:52