The chemical polymerization of pyrryl Mannich base methiodide salt to porphyrins

Er, Song-Swee (1974) The chemical polymerization of pyrryl Mannich base methiodide salt to porphyrins. Masters thesis, Memorial University of Newfoundland.

[img] [English] PDF (Migrated (PDF/A Conversion) from original format: (application/pdf)) - Accepted Version
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.

Download (19Mb)
  • [img] [English] PDF - Accepted Version
    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.
    (Original Version)

Abstract

Pyrryl Mannich base methiodides were polymerized in both anhydrous hydroxylic and nonhydroxylic solvents with the hope of clarifying some aspects of the mechanism of porphyrin formation. Although a mixture of type isomers were obtained, the product composition was found to consist of ~ 95% type (III and IV) and ~ 5% type (I and II) isomers from various solvents. The results suggested that the isomer composition is not dependent on the presence of “active” hydrogen in the solvent, and polymerization is not due to separation of formaldehyde (or equivalent) from the pyrrole and then a “random” polymerization; formation of type III and IV porphyrins is an inherent property of trimethylaminopyrrole salts and rearrangement in some form is a normal part of polymerization. On the basis of these results and published data, an intermediate with ring D porphobilinogen unit in the pyrrolenine form at right angles to the macrocycle formed from the other three pyrrole units and methane bridges is suggested and a scheme for the natural type III porphyrin formation is also proposed. -- A new compound diethyl 2,5-dimethyl-3,6-pyrazine-dithiolcarboxylate is reported as a by-product of a pyrryl thiolester synthesis.

Item Type: Thesis (Masters)
URI: http://research.library.mun.ca/id/eprint/4260
Item ID: 4260
Additional Information: Bibliography: leaves 52-55.
Department(s): Science, Faculty of > Chemistry
Date: 1974
Date Type: Submission
Library of Congress Subject Heading: Pyrroles; Porphyrins; Polymerization; Salts

Actions (login required)

View Item View Item

Downloads

Downloads per month over the past year

View more statistics