Submitted to: Great Lakes Regional American Chemical Society Symposium
Publication Type: Abstract only
Publication Acceptance Date: 8/15/2004
Publication Date: 10/17/2004
Citation: Knothe, G.H. 2004. Synthesis and characterization of some oxygenated long-chain compounds [abstract]. Great Lakes Regional American Chemical Society Symposium. p. 186. Interpretive Summary:
Technical Abstract: The double bonds in unsaturated fatty compounds offer the opportunity for synthesizing a variety of derivatives. The selenium dioxide/- tert. butylhydroperoxide system, usually used for mono-allylic hydroxylations, also yields allylically dihydroxylated compounds (2(E)-ene-1,4-diols) as erythro / threo diastereomers when reacted with monounsaturated fatty compounds besides the expected monohydroxylated species. When reacting such fatty compounds with SeO2 / H2O2, cyclic selenites can be isolated as intermediates in the formation of vicinal diols. This presentation discusses the synthesis and the characterization of these and related materials, especially by NMR.