Subbiliazine: A Contracted Phthalocyanine Analog

The direct borylation of two bis­(pyrazolylimino)­isoindoline chelates with BF3 and base under dry conditions results in the formation of two boron adducts. These are ring-contracted analogs of biliazine and can be considered as subbiliazines, as they have bowl-shaped structures similar to subphthal...

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Bibliographic Details
Published in:Organic letters 2021-02, Vol.23 (3), p.1076-1080
Main Authors: Schrage, Briana R, Nemykin, Victor N, Ziegler, Christopher J
Format: Article
Language:English
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Summary:The direct borylation of two bis­(pyrazolylimino)­isoindoline chelates with BF3 and base under dry conditions results in the formation of two boron adducts. These are ring-contracted analogs of biliazine and can be considered as subbiliazines, as they have bowl-shaped structures similar to subphthalocyanine. Additionally, a new iminooxoisoindoline BF2 complex was made from hydrolysis of the free base in the presence ofBF3. The electronic structures of the free bases and subbiliazines were probed by density functional theory (DFT) and time-dependent DFT (TDDFT) methods.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c04291