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Molecules 2002, 7(3), 341-352; doi:10.3390/70300341
Article

Synthesis and Rearrangement of 3-Methyl-1,4-pentadiyne-3-ol

, ,  and *
Roche Vitamins Ltd., Vitamins Research and Technology Development, Grenzacherstr., CH-4070 Basel, Switzerland
* Author to whom correspondence should be addressed.
Received: 8 March 2002 / Revised: 26 March 2002 / Accepted: 27 March 2002 / Published: 31 March 2002
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Abstract

An efficient synthesis and rearrangement of 3-methyl-1,4-pentadiyne-3-ol (1) using perrhenate- and Mo(VI)-catalysts is reported. The by-products 3,6-dimethyl-1,4,7-octatriyne-3,6-diol (2) and 3-ethynyl-5-methyl-1,6-heptadiyne-3,5-diol (3) were isolated and spectroscopically characterized. A possible reaction mechanism for the formation of the byproducts is discussed.
Keywords: α; β-unsaturated carbonyl compound; α-alkynols; Meyer-Schuster rearrangement; perrhenate-catalysts; Mo(VI)-catalysts α; β-unsaturated carbonyl compound; α-alkynols; Meyer-Schuster rearrangement; perrhenate-catalysts; Mo(VI)-catalysts
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Buser, D.; Pauling, H.; Thum, A.; Bonrath, W. Synthesis and Rearrangement of 3-Methyl-1,4-pentadiyne-3-ol. Molecules 2002, 7, 341-352.

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