Abstract
Tributyltin hydride reaction of the tricyclo[5.2.1.0 2,6]decenes 5, 16 and 23 bearing a halo-carbonyl moiety has been shown to involve CC bond cleavage as the major reaction path leading to bridged eight-membered rings 12, 17 and 24. In contrast the halo-carbonyl derivatives 8, 33 and 36 undergo only reduction of the carbon-halogen bond. The ring cleavage observed has been attributed to the release of strain arising from nonbonded interaction as well as strain associated with norbornene.
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