Radical-induced cyclizations of cis-1,10-dichlorodec-5-ene and 1,10-dichlorodec-5-yne

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.