Isomerization reactions of allylic alcohols into ketones with the Grubbs reagent.
Allylic alcohols were isomerized into ketones by the action of the Grubbs reagent. Some model alcohols were prepared and tested under similar conditions to reveal that less substituted alkenes rearrange more easily. More hindered alcohols are stable under these conditions, however, the simple allylic alcohols tend to isomerize producing ethyl ketone and the corresponding degraded methyl ketone.
Nakashima
Katsuyuki
K
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, 770-8514, Japan.
Okamoto
Sanae
S
Sono
Masakazu
M
Tori
Motoo
M
D007202:Indicators and Reagents; D007536:Isomerism; D007659:Ketones / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*
D007202:Indicators and Reagents; D007659:Ketones; D009942:Organometallic Compounds; D020005:Propanols; C524958:bis(trichlorohexylphosphine)benzylideneruthenium; C006463:allyl alcohol