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Mechanistic investigation of the boron alkylidene/alkene cycloaddition reaction. (a) Isotope labeling studies support the intermediacy of a four-membered boretane. (b) Stereochemical and radical clock experiments suggest that radical intermediates may not be involved. (c) Use of a labeled alkene suggests the 2+2 reaction is not a stereospecific process. (d) The lack of stereospecificity in 2+2 reactions enables stereoconvergent reactions.
