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The Oxidation Of Monocyclic Pyrroles

G. Gardini
Published 1973 · Chemistry

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Publisher Summary Pyrroles are unstable in the presence of oxygen. In particular alkylpyrroles undergo rapid autoxidation on exposure to air, even in absence of light. This chapter is a review of reported work of pyrrole nucleus. The literature of the oxidation of pyrroles does not yet provide a clear general picture of the behavior of the pyrrole nucleus toward oxygen and other oxidizing agents. The only generalities that can be discerned are: Pyrroles being very activated toward electrophilies in the α positions, the attack by oxidants proceeds exclusively in those positions, or in the side chain if both α positions are occupied; in strongly acidic media pyrrole blacks are the main products from 2,5-unsubstituted substrates, while brown tars and syrups are formed from other pyrroles; in weakly acidic or basic media, in water or organic solvents, simple oxidation products (unsaturated γ-lactams, maleimides, and succinimides) are obtained from aIkylpyrroles, while aryl derivatives often undergo ring opening; and electron-withdrawing groups on the pyrrole ring show a strong stabilizing effect toward oxidation. The chapter discusses autoxidation, photo-oxidation, and oxidation by chemical reagents, and such. The oxidation mechanisms need much more research to be well defined; at present only the photo-oxidation mechanism has been studied in any detail.
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