Intramolecular Interaction of Adjacent Hydroxymethyl, Formyl, and Carboxyl Groups: Proximity Effect in the Swern Oxidation of cis,cis-1,3,5-Tris(hydroxymethyl)-1,3,5-trimethylcyclohexane

Article abstract of DOI:10.1021/jo990468o

The proximity effect in the Swern oxidation of cis,cis-1,3,5-tris(hydroxymethyl)-1,3,5-trimethylcyclohexane (4) with TFAA was examined. The oxidation reaction of triol 4 with DMSO, TFAA, and relatively small amounts of triethylamine gave 5-formyl-cis,cis-