O-alkylation of menthone oxime: Synthesis and 13C NMR studies of a series of novel oxime ethers

Article abstract of DOI:10.1080/00397910903370691

A series of novel menthone oxime ethers were synthesized in three steps starting from (-)-menthol. Analysis of the 13C NMR chemical shift differences between carbons of oxime derivatives (O-alkyl oximes) provides a convenient and reliable means of assigning oxime stereochemistry. It has been found that carbons syn to the oxime are shifted more upfield than carbons anti to the oxime moiety. Significant E products were obtained. Copyright Taylor & Francis Group, LLC.