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Topic: Sulphonate leaving groups  (Read 2868 times)

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Sulphonate leaving groups
« on: December 03, 2004, 08:10:33 PM »
Why are tosylates, triflates, etc. all more reactive in their corresponding Sn2 reaction in aprotic media (read: THF or Ether) than the iodides?  HI is a stronger acid than tosic acid and therefore I- is a weaker base than TsO-, but the tosylate is about an order of magnitude better leaving group than I-.  Why?


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