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

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