Re2O7-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles

Wantanee Sittiwong, Michael W. Richardson, Charles E. Schiaffo, Thomas J. Fisher, Patrick H. Dussault

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

Re(VII) oxides catalyze the acetalization, monoperoxyacetalization, monothioacetalization and allylation of hemiacetals. The reactions, which take place under mild conditions and at low catalyst loadings, can be conducted using hemiacetals, the corresponding O-silyl ethers, and, in some cases, the acetal dimers. Aldehydes react under similar conditions to furnish good yields of dithioacetals. Reactions of hemiacetals with nitrogen nucleophiles are unsuccessful. 1,2-Dioxolan-3-ols (peroxyhemiacetals) undergo Re(VII)-promoted etherification but not allylation. Hydroperoxyacetals (1-alkoxyhydroperoxides) undergo selective exchange of the alkoxide group in the presence of either Re2O7 or a Brønsted acid.

Original languageEnglish (US)
Pages (from-to)1526-1532
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Volume9
DOIs
StatePublished - Jul 30 2013

Keywords

  • Allylation
  • Hemiacetal
  • O,O-acetal
  • O,S-thioacetal
  • Peroxyacetal
  • Re O
  • S,S-acetal

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Re<sub>2</sub>O<sub>7</sub>-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles'. Together they form a unique fingerprint.

  • Cite this