Mercuric Triflate-Catalyzed Reaction of Propargyl Acetates with Water Leading Vinyl Ketones

…, Y Asai, H Takano, H Hamagaki, M Nishizawa

Index: Imagawa, Hiroshi; Asai, Yumiko; Takano, Hiroto; Hamagaki, Hitomi; Nishizawa, Mugio Organic Letters, 2006 , vol. 8, # 3 p. 447 - 450

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Citation Number: 35

Abstract

Reaction of propargyl acetate with water catalyzed by Hg (OTf) 2 afforded vinyl ketone as the major product along with a dimeric vinyl mercuric product and normal hydration products in small amounts. The reaction is an alternative to the Meyer-Schuster and Rupe rearrangement applicable to primary alcohols, although the mechanism is entirely different.