Advances in Organocopper Chemistry : A New Mixed Cuprate Reagent
Eck, Stephen Louis
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This paper describes the preparation and reactions of two bis-cuprate reagents of the form: Li(PhS)Cu(CH2)nCu(PhS) Li, n = 4,5. These reagents were prepared from the corresponding dilithioalkanes and have been shown to undergo reactions characteristic of cuprates. Benzoyl chloride is converted to the corresponding dibenzoyl-alkane (C6HSCO(CH2)nCOC6HS) by these reagents in good yields. With these reagents, the spiroannelation of 3-chloro-2-cyclohexenone and S,S-dimethyl-3-chloro-2-cyclohexenone has been achieved in a one-step process to produce spiro decanones and spiro undecanones in moderate yields. Further study of these reagents and their application to the synthesis of spirosesquiterpenes is discussed.