TiCl4 induced anti-Markovnikov rearrangement.
Stereoisomeric bicyclic tert-alcohols afforded identical ring-expansion products via cationic anti-Markovnikov rearrangement from perpendicular tert-cations into identical six-membered ring secondary cations by the treatment with TiCl4. These results provide evidence that the reaction takes place by the cationic stepwise mechanism. [reaction: see text]
Nishizawa
Mugio
M
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
Asai
Yumiko
Y
Imagawa
Hiroshi
H
D000438:Alcohols / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D002412:Cations; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
D000438:Alcohols; D001643:Bridged Bicyclo Compounds; D002412:Cations; C025096:titanium tetrachloride; D014025:Titanium