Cyclohexadienyl-Type Cationic Intermediates in the Friedel–Crafts Alkylation of Benzene Derivatives with the 9-Fluorenyl Cation—Observation by Laser Flash Photolysis | Health & Environmental Research Online (HERO)

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Citation
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HERO ID

856880

Reference Type

Journal Article

Title

Cyclohexadienyl-Type Cationic Intermediates in the Friedel–Crafts Alkylation of Benzene Derivatives with the 9-Fluorenyl Cation—Observation by Laser Flash Photolysis

Author(s)

Cozens, F; Li, J; Mcclelland, RA; Steenken, S

Year

1992

Volume

Issue

Page Numbers

743-745

DOI

10.1002/anie.199207431

Web of Science Id

WOS:A1992JG46800012

URL

http://doi.wiley.com/10.1002/anie.199207431
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Abstract

Direct detection of both types of cationic intermediates in an electrophilic aromatic substitution is possible by laser flash photolysis of 9-fluorenol (1) in the presence of arenes like mesitylene (2). The reactions are fast, yet products are formed with selectivities suggestive of a transition state resembling the intermediate cyclohexadienyl cation ("sigma-complex") and not a "pi-complex".