Influence of strain on chemical reactivity. Relative reactivity of torsionally strained double bonds in 1, 3-dipolar cycloadditions
KJ Shea, JS Kim
Index: Shea, Kenneth J.; Kim, Jang-Seob Journal of the American Chemical Society, 1992 , vol. 114, # 12 p. 4846 - 4855
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Citation Number: 53
Abstract
Abstract: The addition of picryl azide to a series of mono-and bicyclic olefins including trans- cycloalkenes and bridgehead alkenes is reported. Secondary reaction products were identified, and their mechanism of formation was explained by an analysis relating the transition state energies to the conformation of the reaction intermediates. Bridgehead alkenes showed reversed regiochemistry of cycloaddition when compared with model ...
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