Publication

The investigation of methylmagnesium chloride as a non-nucleophilic base

Gbadebo, Omolola
Thumbnail Image
Files
Thumbnail Image
2019Gbadebophd.pdf
Adobe PDF, 15.53 MB
Repository DOI
Publication Date
2018-11-30
Keywords
Grignard reaction, Nitriles, Alkylation, Magnesium bases, Amides, Chemistry, Science
Type
Thesis
Downloads
Show all metadata
Citation
Abstract
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.
Funder
Publisher
NUI Galway
Publisher DOI
Rights
Attribution-NonCommercial-NoDerivs 3.0 Ireland
cbn
Collections
University of Galway Theses (PhD Theses)