A novel elimination reaction

Paterson, William Gilchrist (1965) A novel elimination reaction. PhD thesis, University of Glasgow.

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An elimination reaction leading to iminos was reported in 1926, by Holmes and Ingold, who isolated benzylidene methylamine (II) after fusing the sulphonamide (I) with moist potassium hydroxide. One became interested in the reaction as a means of introducing carbon-nitrogen double bonds into heterocyclic rings. A study of the literature suggested that a successful elimination reaction leading to anils would require mild basic conditions, and the presence of electron-withdrawing groups on the carbon atom adjacent to the nitrogen atom. A preliminary investigation6 proved the validity of this forecast: anils (III: R=Ph; R'=C6H4.NO2-p ot CO.Ph) were obtained in high yield, on treating sulphonamides (IV: R=Ph; R'=C6H4.NO2-p or CO.Ph) with sodium methoxide in toluene at room temperature; sulphonamides such as (IV: R=Ph; R'=CH3. or Ph.) failed to react, even with very strong bases. It remained to demonstrated the utility of the reaction in the synthesis of certain novel heterocyclic systems: 1. The synthesis of an azetropone: When treated with aluminium chloride in chloroform at -70

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Additional Information: Adviser: G R Proctor
Keywords: Organic chemistry
Date of Award: 1965
Depositing User: Enlighten Team
Unique ID: glathesis:1965-72188
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 24 May 2019 15:11
Last Modified: 24 May 2019 15:11
URI: https://theses.gla.ac.uk/id/eprint/72188

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