X-Nico

2 unusual facts about Saul Winstein


2-Norbornyl cation

First reports of its formation and reactivity published by Saul Winstein sparked controversy over the nature of its bonding, as he invoked a three-center two-electron bond to explain the stereoselectivity of the resulting product.

In 1949, Saul Winstein observed that 2-exo-norbornyl brosylate (p-bromobenzenesulfonate) and 2-endo-norbornyl tosylate (p-toluenesulfonate) gave a racemic mixture of the same product, 2-exo-norbornyl acetate, upon acetolysis (see Figure 6).



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