Self-Promoted Nucleophilic Addition of Hexafluoro-2-propanol to Vinyl Ethers

In spite of its low nucleophilicity, hexafluoro‐2‐propanol easily adds to vinyl ethers, without catalyst, to afford a range of hexafluoroisopropyloxy acetals. This addition reaction also occurred in the presence of a competitive, more nucleophilic alcohol. Kinetic studies showed the importance of hy...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2006-01, Vol.348 (1-2), p.118-124
Main Authors: Di Salvo, Andrea, David, Marc, Crousse, Benoît, Bonnet-Delpon, Danièle
Format: Article
Language:English
Subjects:
acetals
carbohydrates
fluorine
hexafluoro-2-propanol
protecting groups
solvent effect
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Summary:In spite of its low nucleophilicity, hexafluoro‐2‐propanol easily adds to vinyl ethers, without catalyst, to afford a range of hexafluoroisopropyloxy acetals. This addition reaction also occurred in the presence of a competitive, more nucleophilic alcohol. Kinetic studies showed the importance of hydrogen bond parameters in the rate and course of the reaction.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200505260