Sulfimidation of thio-ether crown systems: The X-ray crystal structure of the {[9-ane]S(2)S(NH(2)}(+), {[9-ane]SS(NH(2))S(NH(2))}(2+), and

Treatment of the thio-ether crown [9-ane]S3 (1) with 1 equiv of O-mesitylsulfonylhydroxylamine (MSH) yields the water-soluble protonated sulfimide {[9-ane]S2S(NH2)}+ (2). Two equiv of MSH leads to the formation of {[9-ane]SS(NH2)S(NH2)}2+ (3), while excess MSH generates the {[9-ane]S(NH2)S2(m-N)}2+ cation (4) (2-4 form as salts of the [Me3C6H2SO3]- anion); the X-ray crystal structure of 2 and 3 confirms that one and two of the ring sulfurs, respectively, have been converted to terminal protonated sulfimides, while that of 4 reveals the presence of both terminal and bridging nitrogens.