A general, selective synthesis of ω-hydroxyethenyl ethers
A general selective synthesis of β-, γ- and δ-hydroxyethenyl ethers, a class of compounds containing two mutually reactive functionalities positioned at an interacting distance, is based on the reaction of diols with 1,2-bis-(phenylsulfonyl)ethylene (BPSE) followed by reductive elimination of the resulting β-phenylsulfonyl acetals with sodium amalgam.
Reductive opening of carbohydrate phenylsulfonylethylidene (PSE) acetals
The phenylsulfonylethylidene (PSE) acetal is a relatively new protecting group in carbohydrate chemistry. However, carbohydrate-derived phenylsulfonylethylidene (PSE) acetals show a different behavior in reductive desulfonylation than simple symmetrical a
Chéry, Florence,Cabianca, Elena,Tatibou?t, Arnaud,De Lucchi, Ottorino,Lindhorst, Thisbe K.,Rollin, Patrick
p. 117 - 124
(2015/10/28)
Nucleophilic addition to acetylenes in superbasic catalytic systems: XIV. Vinilation of diols in a system CsF-NaOH
A new catalytic system CsF-NaOH was developed for the synthesis of mono- and divinyl ethers of alkanediols exceeding in efficiency KOH. The nucleophilic addition of diols to acetylene in the presence of this system occurs both at enhance pressure (without solvent, 140-160°C) and atmospheric pressure (in DMSO medium, 100°C) of acetylene. Conditions were established of a selective preparation in a high yield of divinyl ethers from diols. 2005 Pleiades Publishing, Inc.