[C:1]1(=O)[CH2:4][CH2:3][CH2:2]1.[C:6]([S:10]([NH2:12])=[O:11])([CH3:9])([CH3:8])[CH3:7]>O1CCCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[C:1]1(=[N:12][S:10]([C:6]([CH3:9])([CH3:8])[CH3:7])=[O:11])[CH2:4][CH2:3][CH2:2]1A mixture of titanium (IV) ethoxide (22.4 mL, 107 mmol) and cyclobutanone (5.37 mL, 71.0 mmoL) in tetrahydrofuran (120 mL) was stirred for 10 minutes. Tert-butanesulfinamide (7.17 g, 59.0 mmol) was added and the reaction mixture was stirred at room temperature for 18 hours. The mixture was concentrated and the residue dissolved in ethyl acetate. The solution was washed with saturated aqueous sodium hydrogen carbonate, dried over sodium sulphate and concentrated to give N-cyclobutylidene-2-methylpropane-2-sulfinamide (9.51 g, 77%) as a pale yellow oil which was used directly without purification.
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