Synthesis of pyrrole derivatives related to the uroporphyrins.

Chen, Teng-song (1967) Synthesis of pyrrole derivatives related to the uroporphyrins. Masters thesis, Memorial University of Newfoundland.

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Abstract

The biosynthesis of tetrapyrroles is briefly discussed and the important intermediates for chemical synthesis of these compounds are derived by valuable new methods. -- Desulfurization of the pyrrole thiolesters was investigated, and the column reaction was introduced to improve the yield of the products. -- Pyrrole aldehydes, hydroxymethyl pyrroles, and methyl pyrroles could be obtained from the corresponding pyrrole thiolesters in fairly good yields. -- The hydroxymethyl group on pyrrole ring is easily converted to methyl group through chloromethyl group. Both β-hydroxymethyl pyrroles and β-chloromethyl pyrroles are easily converted to β, β¹-dipyrromethanes in acidic medium. -- N-H stretching of α-carbethoxydipyrromethanes is very similar to that of α-carbethoxypyrroles, and shows strong intermolecular hydrogen bonding in nonpolar solvents. α, α¹-Dipyrromethanes which have adjacent oarbethoxy groups show intramolecular hydrogen bonding where as β, β¹-dipyrromethanes do not. -- Infrared, ultraviolet and nuclear magnetic resonance spectra are given for all the new compounds.

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