Premium
Surprising Outcomes of Classic Ring‐Expansion Conditions Applied to Octaethyloxochlorin, 1. Baeyer–Villiger‐Oxidation Conditions
Author(s) -
Li Ruoshi,
Zeller Matthias,
Brückner Christian
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601422
Subject(s) - chemistry , pyrrole , porphyrin , ketone , ring (chemistry) , chromophore , reactivity (psychology) , combinatorial chemistry , block (permutation group theory) , baeyer–villiger oxidation , oxide , organic chemistry , catalysis , medicine , alternative medicine , geometry , mathematics , pathology
The conversion of synthetic porphyrins to derivatives that contain a nonpyrrolic building block is an appealing method to generate porphyrinoids with functional groups at their periphery for sensing applications or chromophores with fine‐tuned electronic properties for a number of technical and biomedical applications. Baeyer–Villiger oxidations are potentially suited to generate such pyrrole‐expanded porphyrinoids from known octaethyloxochlorin. However, the application of different Baeyer–Villiger‐oxidation conditions to this ketone merely led to the formation of novel and known compounds, such as porphyrinic meso ‐OH and N ‐oxide derivatives. This work demonstrates how the extraordinary structural stability of the porphyrin macrocycle redirects the reactivity patterns of classic ring‐expansion reactions, which outlines some limits of the methods to convert a pyrrole in porphyrins into a nonpyrrolic building block.