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- Title
First isolation of a Wheland intermediate in the azo-coupling reaction, its X-ray crystal structure determination and products from its evolution.
- Authors
Boga, Carla; Del Vecchio, Erminia; Tozzi, Silvia; Forlani, Luciano; Monari, Magda; Micheletti, Gabriele; Zanna, Nicola
- Abstract
The reaction between tris(N-piperidinyl)benzene and 4-methoxybenzenediazonium tetrafluoroborate afforded a Wheland intermediate (W) that was isolated and crystallized at low temperature. This permitted to obtain, for the first time, the X-ray structure analysis of a s- complex in the diazo coupling reaction. In solution, W slowly evolves to the rearomatized product PH+ (as salt). The single crystal X-ray diffraction determination of the neutral azo compound P is also reported.
- Subjects
CYCLOHEXADIENYL cations; AZO compounds; COUPLING reactions (Chemistry); CRYSTAL structure; BENZENE; TETRAFLUOROBORATES
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2014, p51
- ISSN
1551-7004
- Publication type
Article
- DOI
10.3998/ark.5550190.p008.311