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Updated: Feb 13, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
Regioselective Oxidative Ring Cleavage of a Phlorin Analogue: An Approach for Synthesizing Linear Tetrapyrroles
Jiewei Shao1, Chengjie Li1, Jiahui Kong1
1Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering , East China University of Science and Technology , Shanghai 200237 , China.
Abstract:
Oxidation of neo-N-confused phlorin 1 with excessive FeCl3 leads to regioselective ring opening, generating three linear tetrapyrroles, i.e., (10 Z,15 Z)-biladienone 2, (10 Z,15 E)-biladienone 3, and 19-methoxy (10 Z,15 E)-biladiene 4 with an overall yield of 88%. The coordination of these compounds with Zn(II) is affected by the inverted terminal pyrrolic unit, and the presence of the electron-withdrawing keto moiety. The structural identities were also clearly elucidated by the crystal structures of 3 and 4-Zn and were rationalized by DFT calculations.
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