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New Transformations Involving Squarate Esters. Multi-Channel Rearrangement Options Available To 2-(Dimethoxy-Methyl)-1-Cycloalken-1-Yl Adducts‡

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The Vilsmeier-Haack reaction of cyclic ketones with PBr3 and DMF is an effective means for generating β-bromo-α,β-unsaturated aldehydes, which are readily transformed into their dimethyl acetals. These bromides are conveniently amenable to halogen-metal exchange in the presence of tert-butyllithium. The resultant organometallic intermediates, when treated with an equimolar amount of diisopropyl squarate, undergo 1,2-addition to deliver α-hydroxy ketone adducts that have proven to be sensitive to different rearrangements when in the presence of silica gel or boron trifluoride etherate. Although both processes involve net ring expansion of the cyclobutene ring with loss of methanol, the similarity stops there. In the first instance, spirocyclic diketones are produced by 1,2-shift of either of two ring carbons. In the second, extensively conjugated lactones are generated. The behavior of the adduct originating from a lithiated quinone bisketal has also been scrutinized.

Affiliations: 1: Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210 USA


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