Oxidation of furans with dimethyldioxirane. Interception of malealdehyde and related aldehydes via Wittig reactions
作者:Brian J. Adger、Collette Barrett、Joseph Brennan、Peter McGuigan、M. Anthony McKervey、Brian Tarbit
DOI:10.1039/c39930001220
日期:——
Unsaturated aldehydes including malealdehyde, generated in acetone by oxidation of furans with dimethyldioxirane, can be trapped efficiently by phosphoranes in Wittig reactions.
The title compounds 1 were synthesized from the mono-diEt-acetal of acetylenedicarbaldehyde and 2-thioxo-1,3-dithioles through three key steps: cycloaddition, dimerization-desulphurization of the resulting thials, and after deketalization, fourfold Wittig olefination of the tetraformyl TTF-vinylogs 4 with the P-ylids Walpha-gamma bearing the 1,3-dithiol-2-ylidene moiety. Cyclic voltammetry shows that these compounds are very strong pi-donors and good precursors of conducting cation-radical salts.