Synthesis of enantiomeric menthol derivatives for forming and probing chiral surfaces. X-ray crystal and molecular structures of (+)-(1S,2R,5S)-1-(2-tricyanovinyl-1H-pyrrol-1-yl-methoxy)-2-isopropyl-5-methylcyclohexane

Two enantiomeric pairs of menthol derivatives, the menthol ester with 10-undecynoic acid and the 2-tricyanovinyl-pyrrole derivative of the methoxy-menthol, have been synthesized and their pure enantiomers obtained. The X-ray crystal and molecular structure of the (+)-enantiomer of the latter compound is reported.

Graphical abstractThe product is both homochiral and electroactive showing a quasi-reversible cyclic voltammetry.Figure optionsDownload full-size imageDownload as PowerPoint slide

(+)-(1S,2R,5S)-1-(2-tricyanovinyl-1H-pyrrol-1-yl-methoxy)-2-isopropyl-5-methylcyclohexaneC20H24N4O[α]D20 = +4.2 (c 1.5, CHCl3)

(+)-(1S,2R,5S)-1-(10-undecynoate)-2-isopropyl-5-methylcyclohexaneC21H36O2[α]D20 = +4.7 (c 1.5, CHCl3)