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Mechanistic Rationalization of Unusual Sigmoidal Kinetic Profiles in the Machetti–De Sarlo Cycloaddition Reaction

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journal contribution
posted on 18.02.2015, 00:00 by Matthew P. Mower, Donna G. Blackmond
Unusual sigmoidal kinetic profiles in the Machetti–De Sarlo base-catalyzed 1,3-dipolar cycloaddition of acryl­amide to N-methyl­nitro­acet­amide are rationalized by detailed in situ kinetic analysis. A dual role is uncovered in which a substrate acts as a precursor to catalyze its own reaction. Such kinetic studies provide a general protocol for distinguishing among different mechanistic origins of induction periods in complex organic reactions.