Published in
Royal Society of Chemistry, Organic Chemistry Frontiers, 22(10), p. 5579-5591, 2023
DOI: 10.1039/d3qo00811h
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Why is phenyl azide so unreactive in [3 + 2] cycloaddition reactions? Demystifying Sustmann's paradigmatic parabola
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Abstract
Phenyl azide only participates in [3 + 2] cycloaddition reactions with strongly nucleophilic enamines. A good correlation between the polar character of the reaction and the relative reaction rate constants kr is found.