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

Author(s): Dominik Buser | Horst Pauling | Andreas Thum | Werner Bonrath

Journal: Molecules ISSN 1420-3049
Volume: 7; Issue: 3; Start page: 341; Date: 2002;
Original page

Keywords: α | β-unsaturated carbonyl compound | α-alkynols | Meyer-Schuster rearrangement | perrhenate-catalysts | Mo(VI)-catalysts

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.