Intercalation of Multiple Carbon Atoms between the Carbonyls of α-Diketones

…, J Méndez-Andino, RM Arbit, LA Paquette

Index: Balskus; Mendez-Andino; Arbit; Paquette Journal of Organic Chemistry, 2001 , vol. 66, # 20 p. 6695 - 6704

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Citation Number: 44

Abstract

The reaction of open-chain or cyclic α-diketones with specific ω-alkenyl organometallics leads readily under the proper conditions to 1, 2-diols bonded to terminal olefinic chains. With 1-phenyl-1, 2-propanedione, biacetyl, and cyclohexane-1, 2-dione, allylindation in aqueous THF proceeds readily at both adjacent carbonyls. For cyclododecane-1, 2-dione, recourse must be made to allylmagnesium bromide for completing the second-stage ...