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- Title
Skeletal Transformation Triggered by C−F Bond Activation after Photochemical Rearrangement of Fluorinated [7]Helicenes.
- Authors
Matsuda, Chikako; Igarashi, Ryo; Katagiri, Hiroshi; Murase, Takashi
- Abstract
Tri‐ and tetra‐fluorinated [7]helicenes are photolabile and undergo a double fluorine atom transfer. Herein, we show that the transferred product further undergoes a skeletal transformation on silica gel. The transformation begins with activation of the allylic C−F bond on the silanol surface. Then, the resulting carbocation readily undergoes a regioselective nucleophilic aromatic substitution with water, depending on the position of the fluorine substituents. Hexafluoro‐2‐propanol also activated the allylic C−F bond and acted as a nucleophile. These findings support the generation of a highly reactive cationic electrophilic intermediate in the successive transformations involving fluorine atoms.
- Subjects
HELICENES; SILICA gel; CARBOCATIONS; FLUORINE
- Publication
Chemistry - A European Journal, 2022, Vol 28, Issue 19, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202200132