The preparation and properties of some pyrrole aldehydes

Nagy, Hugh (1970) The preparation and properties of some pyrrole aldehydes. Masters thesis, Memorial University of Newfoundland.

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    Available under License - The author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission.
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Abstract

The anomalous physical and chemical properties of 2-pyrrolecarbaldehyde are discussed. The preparation of 3-pyrrolecarbaldehyde was carried out on an increased scale, and the properties of this compound were investigated, especially in comparison to 2-pyrrolecarbaldehyde. The chemical properties of the two compounds were similar. 1-Methyl-3-pyrrolecarbaldehyde was prepared; in some reactions it resembled 3-pyrrolecarbaldehyde. The Wolff-Kishner reductions of the aldehydes gave good yields of the corresponding methyl compounds. Reactions were attempted using a protecting acetal group on some aldehydes, but these failed as the acetals were unstable. -- The ultraviolet spectra of 2- and 3-pyrrolecarbaldehydes obeyed the Beer-Lambert law and there was no evidence of association. The nuclear magnetic spectra, contrary to expectations, did not show long-range spin coupling to the aldehydic proton. The mass spectra of some new compounds are recorded. A suggested fragmentation pattern is given for 2-pyrrolecarbaldehyde, 3-pyrrolecarbaldehyde, l-methylpyrrole-2-carbaldehyde and 1-methylpyrrole-3-carbaldehyde.

Item Type: Thesis (Masters)
URI: http://research.library.mun.ca/id/eprint/7282
Item ID: 7282
Additional Information: Bibliography: leaves [55]-61.
Department(s): Science, Faculty of > Chemistry
Date: 1970
Date Type: Submission
Library of Congress Subject Heading: Aldehydes

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