lsyc_a_912330_sm2104.pdf (1.34 MB)
Acid-Catalyzed Transacetalization from Glycol to Pinacol Acetals
Version 4 2014-08-25, 13:59
Version 3 2014-08-25, 13:59
Version 2 2014-08-18, 14:07
Version 1 2014-08-25, 13:59
journal contribution
posted on 2014-08-25, 13:59 authored by Yvonne Seeleib, Gregor Nemecek, Dominik Pfaff, Bastian D. Süveges, Joachim PodlechA one-pot transacetalization of glycol acetals, frequently used as protecting groups of the aldehyde function, into the more stable pinacol acetals is given. A clean transformation of aromatic and aliphatic substrates is possible with trifluoroacetic acid within 30 min at 0 °C. Glycol acetals derived from ketones (ketals) cannot be converted with this protocol. Deprotection of the pinacol acetals is possible with trifluoromethanesulfonic acid in the presence of water.
