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Isomerization Reactions of Allylic Alcohols into Ketones with the Grubbs Reagent

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Author(s): Katsuyuki Nakashima | Sanae Okamoto | Masakazu Sono | Motoo Tori

Journal: Molecules
ISSN 1420-3049

Volume: 9;
Issue: 7;
Start page: 541;
Date: 2004;
Original page

Keywords: Grubbs reagent | allylic alcohol | isomerization | ketone.

ABSTRACT
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.