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- Title
New Insights into the Hexaphenylethane Riddle: Formation of an α, o-Dimer.
- Authors
Uchimura, Yasuto; Takeda, Takashi; Katoono, Ryo; Fujiwara, Kenshu; Suzuki, Takanori
- Abstract
Upon reduction of a 1 H-cyclobuta[ de]naphthalene-4,5-diylbis(diarylmethylium) species, a new CC bond is formed between the Cα and C ortho atoms of the two chromophores, which presents an unprecedented coupling pattern for the dimerization of two trityl units. By attaching an annulated cyclobutane ring at the opposite peri position of the naphthalene core, the distance between the Cα carbon atoms was elongated beyond the limit of σ-bond formation through 'scissor effects'. The suppression of CαCα bond formation, which would lead to hexaphenylethane-type compounds, is key to the first successful isolation of the α, o-adducts. The 5-diarylmethylene-6-triarylmethyl-1,3-cyclohexadiene unit in the α, o-adducts is stable, and isomerization of the cyclohexadiene unit into an aromatic system was not observed. The newly formed CαC ortho bond was cleaved upon two-electron oxidation to regenerate the dicationic dye.
- Subjects
BOND formation mechanism; CYCLOBUTANE; COUPLING reactions (Chemistry); CHROMOPHORES; ISOMERIZATION; AROMATICITY
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 13, p4082
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201500122