Highly efficient organic reactions "on water", "in water", and both

Nelly Shapiro*, Arkadi Vigalok

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

177 Scopus citations

Abstract

(Chemical Equation Presented) Wet, wet, wet: Hydrophobic aldehydes are cleanly oxidized upon stirring with water in air. Addition of hydrophobic isocyanides to aqueous suspensions of such aldehydes results in the formation of Passerini reaction products, with the aldehyde being the source of both carbonyl and ester functions. Partially watersoluble reagents reacted slower than water-insoluble ones. Isotope labeling studies show that water participates in these "on water" reactions.

Original languageEnglish
Pages (from-to)2849-2852
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number15
DOIs
StatePublished - 31 Mar 2008

Keywords

  • Aldehydes
  • Green chemistry
  • Oxidation
  • Passerini reaction
  • Water

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