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Synthesis and Rearrangement of 3-Methyl-1,4-pentadiyne-3-ol
Roche Vitamins Ltd., Vitamins Research and Technology Development, Grenzacherstr., CH-4070 Basel, Switzerland
* Author to whom correspondence should be addressed.
Received: 8 March 2002; in revised form: 26 March 2002 / Accepted: 27 March 2002 / Published: 31 March 2002
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
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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.
Buser D, Pauling H, Thum A, Bonrath W. Synthesis and Rearrangement of 3-Methyl-1,4-pentadiyne-3-ol. Molecules. 2002; 7(3):341-352.
Buser, Dominik; Pauling, Horst; Thum, Andreas; Bonrath, Werner. 2002. "Synthesis and Rearrangement of 3-Methyl-1,4-pentadiyne-3-ol." Molecules 7, no. 3: 341-352.