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Free radical reaction of endo-bromopropylbicyclo[4.2.0]oct-2-en-7-one 1 leads to deep-seated rearrangement and formation of the bridged tricyclic ketone 2. An authentic sample of 2 was prepared. Reaction of endobromoethylbicyclo[4.2.0]oct-2-en-7-one 18 generates an analogous bridged tricyclic ketone 20 together with cis-bicyclo[4.4.0]decenone 22. Experiments using Bu 3 SnD were carried out to explore the mechanism of the transformation leading to 22.