Journal Article Novel One-Pot Synthetic Method for Propargyl Alcohol Derivatives from Allyl Alcohol Derivatives

Kutsumura, Noriki  ,  Inagaki, Mai  ,  Kiriseko, Akito  ,  Saito, Takao

47 ( 13 )  , pp.1844 - 1850 , 2015-07 , Georg Thieme Verlag
An efficient one-pot procedure for the synthesis of propargyl alcohol derivatives from allyl alcohol derivatives has been developed. The key to this transformation from a C–C double bond to a C–C triple bond is that hydrogen bromide elimination from 1,2-dibromoalkanes that contain a neighboring oxygen functional group is promoted by the inductive electron-withdrawing effect of the oxygen functional group. In the one-pot reaction, tetrabutylammonium hydroxide was the best base, and the addition of molecular sieves 13X also promoted the reaction.

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