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Since the hypervalent twist followed by reductive elimination is a generalreaction pattern for hypervalent iodine reagents, mechanistic studies about thehypervalent twist step provide significant guidance for experiments. Ourprevious work showed there are two types of hypervalent twist models, i.e.apical twist and equatorial twist. We applied both hypervalent twist models toexplain the isomerization mechanism of two important electrophilictrifluoromethylating reagents, Togni I and Togni II. To the best of ourknowledge, there are less detailed studies about the different twist modesbetween both reagents, which are important to predict the right reactionmechanism and especially, understand well the differences of reactivity andstability. Here, we successfully identified Togni II's isomerization pathwayvia equatorial twist, and suggested different hypervalent twist models shouldbe considered to predict the right mechanisms of reactions with hypervalentiodine reagents.

Predicting the Right Mechanism for Hypervalent Iodine Reagents by Applying Two Types of Hypervalent Twist Models: Apical Twist and Equatorial Twist