The radical reduction of cis-1,10-dichlorodec-5-ene and 1,10-dichlorodec-5-yne initiated by tributylstannane was studied. The products consisted of a series of mono-, bi-, and a-cyclic compounds. Formation of the mono-cyclic compound from the alkene proved to be a very ready reaction, consistent with a solvent cage effect.
S. A. Dodson and R. D. Stipanovic, J. Chem. Soc., Perkin Trans. 1, 1975, 410 DOI: 10.1039/P19750000410
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