Control of regioselectivity in reactions of dialkylstannylene acetals. Part I. A dramatic reversal of regioselectivity in mono-p-toluenesulfonation reactions
The regioselectivities of p-toluenesulfonation reactions of dialkylstannylene acetals obtained from a number of carbohydrate-derived terminal 1,2-diols in the absence of added nucleophiles have been explored as functions of the carbohydrate structure, the
Kong, Xianqi,Grindley, T. Bruce
p. 2396 - 2404
(2007/10/02)
Inversion of regioselectivity in reactions of diols through the use of hexamethylenestannylene acetals as intermediates
Hexamethylenestannylene acetals obtained from a variety of carbohydrate-derived terminal 1,2-diols give good to excellent regioselectivity for tosylation at the secondary oxygen. In contrast, non-cyclic dialkylstannylene acetals react mainly at the primary oxygen. These results are attributed to the greater stability of the dominant stannylene acetal dimers for hexamethylenestannylene acetals.
Grindley,Kong
p. 5231 - 5234
(2007/10/02)
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