Home – Home – Jornals – Chemistry for Sustainable Development 2017 number 3

Reactivity data of (R)-4-menthen-3-one and routes of its transformations with the participation of hydride, sulphur and nitrogen-containing reactants were generalized and systematized. An opportunity to prepare a range of new potentially pharmacologically active sulphides, sulphoxides, acetamides and an oxime of the menthane series based on (R)-4-menthen-3-one and its derivatives was demonstrated using the Ritter reaction, nucleophilic and electrophilic thiating, nitrosation, oximation. Resulting from the carried out systematic research of reactions of (R)-4-menthen-3-one and its derivatives with aluminium- and boron-containing hydride reagents, it was detected that i-Bu₂AlH was the most stereospecific hydride reducing agent for (R)-4-menthen-3-one to (1R,3R)-n-menth-4-en-3-ol. It was found that the BH₃ x THF complex was a stereospecific hydride agent for the oxo group of (R)-4-menthen-3-one and regiospecific but a low-stereoselective hydroborating reagent for its multiple bond and that of (1R,3R)-n-menth-4-en-3-ol.