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Synthesis of Curved Polycyclic Arenes Embedded with Oxepine and Thiepine Using Ring Expansion Strategy.
- Source :
-
Organic letters [Org Lett] 2023 Jul 14; Vol. 25 (27), pp. 5027-5032. Date of Electronic Publication: 2023 Jul 03. - Publication Year :
- 2023
-
Abstract
- A tandem oxidative ring expansion of a six- to seven-membered ring was developed to construct a new class of negatively curved polycyclic arenes embedded with oxepine and thiepine, namely, dibenzo[ b , f ]phenanthro[9,10- d ]oxepine (DBPO) and dibenzo[ b , f ]phenanthro[9,10- d ]thiepine (DBPT), respectively. Mechanistic studies disclosed that an unexpected [4 + 2] cycloadduct formed between the alkene moiety of o -biphenyl-linked methylenexanthenes and o -chloranil serves as a radical cation or a dication equivalent that facilitates the FeCl <subscript>3</subscript> -mediated tandem ring expansion process.
- Subjects :
- Oxepins
Subjects
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 25
- Issue :
- 27
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 37395473
- Full Text :
- https://doi.org/10.1021/acs.orglett.3c01730