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Question

What is a tosylate group?


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Solution

Tosylate group:

  • It is a good leaving group.
  • It can be used to convert alcohols into tosylates.
  • Tosylates are good substitution substrates because they react with nucleophiles in the same way as alkyl halides do.
  • Tosylates have a far superior leaving group than the original alcohol:
  • Mesylates (using CH3SO2Cl) and triflates are alternatives to tosylates (using CF3SO2Cl).

Structure of Tosylate group:

methyl tosylate | C8H10O3S | ChemSpider

Properties of Tosylate group:

  • It is generally considered a univalent organic compound.
  • Tosylate are considered as good substrate.

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