Chirality Preservation of a Cation-Radical Intermediate. Tandem Oxidative Ring Expansion-Cyclization Reaction of Optically Active Bicyclo[4.1.0]heptyl Sulfides

1994 ◽  
Vol 59 (17) ◽  
pp. 4727-4729 ◽  
Author(s):  
Yoshiji Takemoto ◽  
Taiichi Ohra ◽  
Hiroki Koike ◽  
Syun-ichirou Furuse ◽  
Chuzo Iwata ◽  
...  
Keyword(s):  
Cation Radical ◽  
Ring Expansion ◽  
Optically Active ◽  
Cyclization Reaction ◽  
Radical Intermediate ◽  
Oxidative Ring Expansion

Access to Optically Active 3-Azido- and 3-Aminopiperidine Derivatives by Enantioselective Ring Expansion of Prolinols

2011 ◽  
Vol 13 (16) ◽  
pp. 4442-4445 ◽  
Author(s):  
Anne Cochi ◽  
Domingo Gomez Pardo ◽  
Janine Cossy
Keyword(s):  
Ring Expansion ◽  
Optically Active

Observation of a radical intermediate in the one electron oxidation of 5-methyl-1-thia-5-azacyclooctane by •Br2−

1984 ◽  
Vol 62 (9) ◽  
pp. 1874-1876 ◽  
Author(s):  
Warren Kenneth Musker ◽  
Parminder S. Surdhar ◽  
Rizwan Ahmad ◽  
David A. Armstrong
Keyword(s):  
Aqueous Solution ◽  
Rate Constant ◽  
Half Life ◽  
Cation Radical ◽  
Order Rate Constant ◽  
Type Structure ◽  
Radical Intermediate ◽  
Text Type ◽  
First Order ◽  
The One

The one electron oxidant •Br2− reacts with 5-methyl-1-thia-5-azacyclooctane (4) in aqueous solution at high pH with an overall rate constant of ~2 × 108 M s−1. The radical intermediate produced has a broad maximum at 500 nm with ε = 2400 M−1 cm−1 and at pH 10 decays with a first order rate constant of 2.3 ± 0.3 × 104 s−1, first half-life of 30 ± 5 μs. Its characteristics do not correspond to those of the [Formula: see text] species reported by Asmus and co-workers. The species appears to be the same as the cation radical reported earlier in the one electron oxidation of 4 in acetonitrile. This species is considered to have an [Formula: see text] type structure, which provides transannular stabilization.

The oxidative ring expansion of spiro-annulated chroman-4-ones: Syntheses of the rotenoid core and related benzoxanthones

1998 ◽  
Vol 39 (8) ◽  
pp. 881-884 ◽  
Author(s):  
Christopher D. Gabbutt ◽  
John D. Hepworth ◽  
B. Mark Heron ◽  
Jean-Luc Thomas
Keyword(s):  
Ring Expansion ◽  
Oxidative Ring Expansion

ChemInform Abstract: Hypervalent Iodine Induced Oxidative Cross Coupling via Thiophene Cation Radical Intermediate.

ChemInform ◽  
2013 ◽  
Vol 44 (18) ◽  
pp. no-no
Author(s):  
Toshifumi Dohi ◽  
Motoki Ito ◽  
Sho Sekiguchi ◽  
Yohei Ishikado ◽  
Yasuyuki Kita
Keyword(s):  
Cation Radical ◽  
Cross Coupling ◽  
Hypervalent Iodine ◽  
Radical Intermediate

Oxidative ring-expansion of benzothiazolines into 1,4-benzothiazines

1981 ◽  
Vol 18 (2) ◽  
pp. 279-282 ◽  
Author(s):  
Gaetano Liso ◽  
Giuseppe Trapani ◽  
Andrea Latrofa ◽  
Paolo Marchini
Keyword(s):  
Ring Expansion ◽  
Oxidative Ring Expansion
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