[OH-:1].[Na+].[S:3]([N:13]1[CH2:16][C:15]([CH2:19][OH:20])([CH2:17][OH:18])[CH2:14]1)([C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].BrBr.[OH2:23]>[Ni](Cl)Cl>[S:3]([N:13]1[CH2:14][C:15]([C:19]([OH:23])=[O:20])([C:17]([OH:1])=[O:18])[CH2:16]1)([C:6]1[CH:7]=[CH:8][C:9]([CH3:10])=[CH:11][CH:12]=1)(=[O:4])=[O:5]Sodium hydroxide (6.3 g) was dissolved in water (50 ml) and nickel chloride (1 g) and N-tosyl-3,3-bis(hydroxymethyl) azetidine (4.4 g) were added. Bromine (9.6 g) was added over 6 hours to the green suspension with vigorous stirring and cooling. The mixture was stirred overnight and the last traces of nickel peroxide destroyed with sodium sulphite. The green precipitate was filtered off and the clear filtrate acidified to pH 1 with hydrochloric acid. Ether extraction yielded the desired product, N-tosylazetidine-3,3-dicarboxylic acid.
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