Butyldimethylsulfonium iodide

Although the sulfur isotope effect is small, its determination might be very useful in studies of reaction mechanisms. This can be shown on the following example the hydrolysis of tert-butyldimethylsulfonium iodide proceeds according to the scheme ... 

Regardless of all these approximations, a valuable mechanistic conclusion can be drawn hydrolysis of tert-butyl iodide is a dissociative process. Since most reactions that produce carbonium ion appear to have transition states closely resembling carbonium ion, it seems reasonable to assume that the isotope effect for the hydrolysis of tert-butyldimethylsulfonium iodide in water is a good approximation of the maximum isotope effect for the C-S bond cleavage. In sharp contrast to this is the very small isotope effect in the E2 reaction of 2-phenylethyldimethylsulfonium bromide with hydroxide ion in water ... 

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See also in sourсe #XX -- [ ]

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