Natural Cyclic α,β‐Enone Monoterpenoids in Nucleophilic Addition Reactions

Abstract

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Influence of electronic structure of (R)-4-menten-3-one on its restricted rotation and inversion

“…Also our calculation data shown that i-Pr group rotation and inversion of cycle in (R)-4-menthen-3-one is restricted [1]. It's unusually, because the same restrictions in other monoterpenoids with similar structure (figure 1) not found [2]. Another unusual fact is increasing of noted restrictions with temperature growing.…”

“…In our previous work [1] we have shown, that uncharacteristic reactivity of (R)-4-menthen-3-one vs. ordinary enone systems [2,3] can be explained by predominant content of one conformer. Also our calculation data shown that i-Pr group rotation and inversion of cycle in (R)-4-menthen-3-one is restricted [1].…”