There are few methods available for the preparation of medium sized cyclic 2-alkynones.  We have recently discovered that ?-oxy-�-hydroxy-a-diazo carbonyl compounds undergo a fragmentation reaction when exposed to tin tetrachloride. To further expand the scope of this reaction, and to apply it toward the synthesis of medium sized cyclic 2-alkynones, we have prepared bicyclic fragmentation precursors such as 2. In this case, the bond that fragments is the ring fusion bond and 9 to 12-membered cyclic 2-alkynones such 3 are formed. Synthetic routes to these bicyclic fragmentation precursors and the results of our fragmentation studies will be discussed.

Preparation of medium sized cyclic 2-alkynones by fragmentation of α-diazo carbonyl compounds

243rd National Meeting (2012)

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