title: Octaethyl-1,3-oxazinochlorin: A β-Octaethylchlorin Analogue Made by Pyrrole Expansion.
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.
authors: †Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
authors: Eileen
authors: E
authors: Meehan
authors: †Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
authors: Ruoshi
authors: R
authors: Li
authors: ‡Department of Chemistry, Youngstown State University, One University Plaza, Youngstown, Ohio 44555-3663, United States.
authors: Matthias
authors: M
authors: Zeller
authors: †Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
authors: Christian
authors: C
authors: Brückner