1,5-Ring closure of 1- or 3-substituted hex-5-enyl radicals affords mainly cis-disubstituted cyclic products, whereas 2- or 4-substituted species give mainly trans-products; the significance of this stereoselectivity is demonstrated in the formation of the norbornane system from acyclic precursors.
A. L. J. Beckwith, T. Lawrence and A. K. Serelis, J. Chem. Soc., Chem. Commun., 1980, 484 DOI: 10.1039/C39800000484
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