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DOI: 10.1055/s-0034-1380499
Novel One-Pot Synthetic Method for Propargyl Alcohol Derivatives from Allyl Alcohol Derivatives
Publication History
Received: 02 February 2015
Accepted after revision: 02 March 2015
Publication Date:
08 April 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201513/lookinside/thumbnails/ss-2015-f0081-op_10-1055_s-0034-1380499-1.jpg)
The paper is dedicated to Professor Amos B. Smith, III, on the occasion of his 70th birthday.
Abstract
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.
Key words
elimination - one-pot synthesis - propargyl alcohol derivatives - allyl alcohol derivatives - neighboring-group effectsSupporting Information
- for this article is available online at http://dx.doi.org/10.1055/s-0034-1380499.
- Supporting Information
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