Cyclobutanone → (1,1'-Bicyclobutyl)-1,1'-diol
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[Cl-].[Li+].[I-].[Sm+2].[I-].[C:6]1(=[O:10])[CH2:9][CH2:8][CH2:7]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[C:6]1([OH:10])([C:6]2([OH:10])[CH2:9][CH2:8][CH2:7]2)[CH2:9][CH2:8][CH2:7]1[Cl-].[Li+].[I-].[Sm+2].[I-].[C:6]1(=[O:10])[CH2:9][CH2:8][CH2:7]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[C:6]1([OH:10])([C:6]2([OH:10])[CH2:9][CH2:8][CH2:7]2)[CH2:9][CH2:8][CH2:7]1To a solution of lithium chloride (2.12 g) in tetrahydrofuran (60 mL) was added samarium(II) iodide (5.0 g) under argon atmosphere, followed by stirring the mixture at room temperature for 15 minutes. To this reaction mixture was added dropwise a solution of cyclobutanone (825 mg) in tetrahydrofuran (5 mL), followed by stirring the mixture at room temperature for 1 hour. To the reaction mixture was added saturated aqueous sodium thiosulfate solution under ice-cooling, followed by extraction with diethyl ether three times. The organic layers were combined, washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 3:2) to give bicyclobutyl-1,1′-diol (399 mg).
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