The stereospecific allylation of vinylstannanes with allylic halides proceeded in the presence of copper(I) iodide in DMSO-THF at room temperature. The stereospecificity of the reaction was dependent on the structures of vinylstannanes and allylic halides, and also the leaving group of allylic halides employed. Concerning the regioselectivity regarding allylic system, higher α-regioselection was observed in the reactions of allylic chlorides than in those of the corresponding iodides.

Direct conversion of methylenebicyclo[4.2.0]octanone to methylenebicyclo[3.2.1]octanol by a Sm(II)-induced 1,2-rearrangement with ring expansion of the methylenecyclobutane is described. Three conditions were optimized to allow the adaptation of this approach to various substrates. A rearrangement mechanism is proposed involving the generation of a ketyl radical and cyclopentanation by ketyl-olefin cyclization, followed by radical fragmentation and subsequent protonation.

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A method is described for synthesizing succinonitrile derivatives bearing alkyl or aryl substituents from cyanohydrin derivatives using low-valent titanium. The active species in this reaction is proposed to be a resonance hybrid of the TiIV nitrile enolate and TiIII alkyl radical.