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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Octaethyl-1,3-oxazinochlorin: A β-Octaethylchlorin Analogue Made by Pyrrole Expansion
Eileen Meehan1, Ruoshi Li1, Matthias Zeller2
1†Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
Abstract:
Treatment of the oxime of octaethyloxochlorin 4, available from octaethylporphyrin 3, under Beckmann conditions provided not the expected lactam, but octaethyl-1,3-oxazinochlorin 8, in which a pyrrole moiety of the parent oxochlorin was expanded by an oxygen atom to an 1,3-oxazinone moiety. Its mechanism of formation was demonstrated to occur along an "abnormal Beckmann" pathway, followed by intramolecular ring closure and hydrolysis. The work expands the methodologies known to convert octaethylporphyrin to pyrrole-modified porphyrin analogues.
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