Highly Efficient Organic Reactions “on Water”, “in Water”, and Both

Abstract

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 water-soluble reagents reacted slower than water-insoluble ones. Isotope labeling studies show that water participates in these “on water” reactions. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z705347_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.