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The allenic ketone 8-methylnonane-1,6,7-trien-4-one and related allenes have been synthesized from simple commercially available materials. Since allenes analogous to 8-methylnonane-1,6,7-trien-4-one have previously been transformed to substituted bicyclo[3.3.0]octanones via corresponding bicyclo[3.2.0]heptanones, it is anticipated that the present allenic ketone may also undergo similar transformations. Substituted bicyclo[3.3.0]octanones are known synthetic precursors of tricyclic sesquiterpenes. Thus, 8-methylnonane-1,6,7-trien-4-one presents itself as a possible precursor for the synthesis of tricyclopentanoid ring system present in sesquiterpenes such as hirsutene and Δ9(12) -capnellene.DOI: http://dx.doi.org/10.4314/bcse.v26i1.11

A protocol has been developed to prepare 1,2-allenyl ketones using molecular oxygen in air or pure oxygen as the oxidant from 2,3-allenylic alcohols with moderate to good yields under mild conditions. In this reaction CuCl (20 mol %) with 1,10-phenanthroline (10 mol %) and bipyridine (10 mol %) was used as the catalyst. It is interesting to observe that the use of the mixed ligands is important for the higher yields of this transformation: With the monoligand approach developed by Markó et al., the yields are relatively lower.

A protocol has been developed to prepare 1,2-allenyl ketones using molecular oxygen in air or pure oxygen as the oxidant from 2,3-allenylic alcohols with moderate to good yields under mild conditions. In this reaction CuCl (20 mol %) with 1,10-phenanthroline (10 mol %) and bipyridine (10 mol %) was used as the catalyst. It is interesting to observe that the use of the mixed ligands is important for the higher yields of this transformation: With the monoligand approach developed by Markó et al., the yields are relatively lower.